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Total synthesis of epothilone B
Figure presented Epothilone A, 1, R = H Epothilone B, 2, R = Me A convergent and stereoselective total synthesis of epothilone B (2) is described. The key steps are Normant reaction, Wadsworth-Emmons reaction of a methyl ketone 14 with the phosphonate reagent 7, diastereoselective aldol condensation of aldehyde 3 with enolate 4 to form the C6-C7 bond, and macrolactonization.
Valluri, Muralikrishna,Hindupur, Rama M.,Bijoy, Panicker,Labadie, Guillermo,Jung, Jae-Chul,Avery, Mitchell A.
p. 3607 - 3609
(2001)
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A novel aldol condensation with 2-methyl-4-pentenal and its application to an improved total synthesis of epothilone B
The stabilization of the transition state through a favorable interaction between the double bond of 1 and the carbonyl group of 2 appears to be responsible for the high diastereoface selectivity of the aldol reaction. This key step in the highly concise total synthesis of epothilone B is followed by a Suzuki coupling to introduce the thiazole domain, a Noyori reduction to control the stereochemistry at C3, and a final macrolactonization (see reaction scheme). X = protecting group.
Balog, Aaron,Harris, Christina,Savin, Kenneth,Zhang, Xiu-Guo,Chou, Ting Chao,Danishefsky, Samuel J.
p. 2675 - 2678
(1998)
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Easy access to the epothilone family - Synthesis of epothilone B
An easy access to four out of five naturally occurring epothilones (A- E, 1-5) is reported. Key steps are an enantioselective Mukaiyama type aldol reaction, (E)- and (Z)-selective olefinations, and a sulfone alkylation.
Mulzer, Johann,Mantoulidis, Andreas,Oehler, Elisabeth
p. 8633 - 8636
(1998)
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Synthesis and conformational analysis of (E)-9,10-dehydroepothilone B: A suggestive link between the chemistry and biology of epothilones
The most potent epothilone analogue reported to date was obtained by incorporation of an E double bond at C9-C10 in the epothilone B series (see picture). Molecular modeling, NMR spectroscopic analysis, and chemical observations were used to rationalize the remarkable potency-enhancing effect of the double bond.
Yoshimura, Fumihiko,Rivkin, Alexey,Gabarda, Ana E.,Chou, Ting-Chao,Dong, Huajin,Sukenick, George,Morel, Florence F.,Taylor, Richard E.,Danishefsky, Samuel J.
p. 2518 - 2521
(2003)
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BLUE LIGHT BLOCKLING SYSTEM CONTAINING PYRAZOLINE OR/AND BENZOIC ACID COMPOUNDS
The present invention relates to an blue light blocking system characterized in that the blue light blocking agents possess the structure of a pyrazoline of the formula (I) or/and a phenylacrylic acid of the formula (II). The compounds of formula (I) or / and formula (II) fully cover the range of short-wavelength blue light to protect eyes; it can also selectively absorb long-wavelength blue light, so that the transmitted light can provide a particularly good visual experience to humans. The invention is applicable to products such as optical films, optical lenses, goggles, skin care, lighting devices, paints, adhesives, or panels. These products have a light-colored appearance and the penetrating light provides an excellent visual experience for humans.
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Paragraph 0029; 0041-0043

(2019/09/17)

PROCESS FOR THE PREPARATION OF (1S,3S,7S,10R,11S,12S,16R)-7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-[(1E)-1-METHYL-2-(2-METHYL-4-THIAZOLYL)ETHENYL]-17-OXA-4-AZABICYCLO[14.1.0]HEPTADECANE-5,9-DIONE AND INTERMEDIATES THEREOF
The present invention relates to an improved process for the preparation of (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2- methyl-4-thiazolyl)ethenyl]- 17-oxa-4-azabicyclo[ 14.1.0]heptadecane-5,9-dione represented by the following structural formula I and intermediates thereof. The present invention also provides novel intermediate compounds useful for the preparation of compound of formula I and its intermediates.
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(2015/06/25)

An efficient total synthesis of (-)-epothilone B
An efficient total synthesis of (-)-epothilone B has been achieved in ca. 8% yield over 11 steps from 9 (or 10 steps from 7/8), which features a bissiloxane-tethered ring closing metathesis reaction to approach the trisubstituted (Z) double bond and forms a new basis for further development of an industrial process for epothilone B and ixabepilone.
Wang, Jie,Sun, Bing-Feng,Cui, Kai,Lin, Guo-Qiang
supporting information
p. 6354 - 6357
(2013/02/23)

Total synthesis of epothilones using functionalised allylstannanes for remote stereocontrol
Two syntheses of the C(7)-C(16)-fragment 41 of epothilone D 2 were developed that were based on tin(iv) bromide mediated reactions of 5,6-difunctionalised hex-2-enylstannanes with aldehydes. In the first synthesis, (5S)-6-tert-butyldimethylsilyloxy-5-hydroxy-2-methylhex-2-enyl(tributyl) stannane 20 was reacted with (E)-but-2-enal to give (2S,7R,4Z,8E)-1-tert- butyldimethylsilyloxy-5-methyldeca-4,8-diene-2,7-diol 26 containing ca. 20% of its (7S)-epimer. Following desilylation, the crystalline (2S,7R)-triol 32 was protected as its acetonide 33 and esterified to give the (4-methoxybenzyloxy) acetate 34. An Ireland-Claisen rearrangement of this ester gave methyl (2R,3S,10S,4E,7Z)-3,7-dimethyl-10,11-(dimethylmethylene)dioxy-2-(4- methoxybenzyloxy)undeca-4,7-dienoate 35 that was converted into (2S,9S,6Z)-2,6-dimethyl-9,10-(dimethylmethylene)dioxydec-6-en-1-ol 41 by regioselective alkene manipulation, ester reduction and cleavage of the resulting terminal diol 40 with a reductive work-up. The second synthesis involved the tin(iv) bromide mediated reaction between the stannane 20 and (3S)-4-(4-methoxybenzyloxy)-3-methylbutanal 44 that gave (2S,7S,9S,4Z)-1-tert- butyldimethylsilyloxy-5,9-dimethyl-10-(4-methoxybenzyloxy)dec-4-ene-2,7-diol 45 containing ca. 20% of its (7R)-epimer. After desilylation and protection of the vicinal diol as its acetonide 46, a Barton-McCombie reductive removal of the remaining hydroxyl group gave the (2S,9S,6Z)-2,6-dimethyl-9,10- (dimethylmethylene)dioxydec-6-en-1-ol 41 after oxidative removal of the PMB-ether. The first of these syntheses uses just one chiral starting material, but the second is shorter and more convergent. It was therefore modified by the use of (5S)-6-tert-butyldimethylsilyloxy-5-(2-trimethylsilylethoxy)methoxy-2- methylhex-2-enyl(tributyl)stannane 49 that reacted with (3S)-4-(4- methoxybenzyloxy)-3-methylbutanal 44 to give a 50:50 mixture of the C(4)-epimers of (2S,9S,6Z)-10-tert-butyldimethylsilyloxy-1-(4-methoxybenzyloxy)-2,6- dimethyl-9-(2-trimethylsilylethoxy)methoxydec-6-en-4-ol 50 with high fidelity for formation of the (Z)-alkene. Following the Barton-McCombie deoxygenation, the product 52 was taken through to (2S,9S,6Z,10E)-2,6,10-trimethyl-11-(2- methyl-1,3-thiazol-4-yl)-9-(2-trimethylsilylethoxy)methoxyundeca-6,10-dienal 59 that corresponded to the fully functionalised C(7)-C(17) fragment of epothilone D 2. A precedented stereoselective aldol condensation followed by O-protection, selective deprotection, oxidation and macrocyclisation then gave the macrolide 71 that was deprotected to complete a synthesis of epothilone D 2. Finally regio- and stereo-selective epoxidation gave epothilone B 1.
Martin, Nathaniel,Thomas, Eric J.
p. 7952 - 7964
(2013/06/27)

FLUORESCENT AGENT HAVING ETHYNYL GROUP
There are provided novel fluorescent agents, such as pyrazoline compounds represented by formula (I): (wherein R1, R2 and R3 are as defined in the specification), having an ethynyl group in the molecule, which have high absorptivity in the ultraviolet-visible short wavelength range (for example, 350 nm-420 nm).
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Page/Page column 6

(2010/12/29)

METHODS, KITS, AND COMPOUNDS FOR DETERMINING RESPONSIVENESS TO TREATMENT OF A PATHOLOGICAL DISORDER BY EPOTHILONES
The invention provides methods, kits and compounds for determining the potential responsiveness of a subject suffering from a pathological disorder, including non-small cell lung cancer (NSCLC), to treatment with an epothilone by analyzing the gene expression profile and/or certain molecular markers in a sample obtained from said subject. The invention further relates to methods, compounds and uses of said compounds for treating subjects suffering from said pathologic disorder, optionally in combination with other therapeutic agents. Also provided are genes and/or proteins encoded by them whose expression level have been determined to differ between epothilone responders and epothilone non-responders.
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(2009/04/24)

Total synthesis of epothilones B and D: Stannane equivalents for β-keto ester dianions
(Chemical Equation Presented) Studies leading to a total synthesis of epothilones B and D are described. The overall synthetic plan was based on late-stage fragment assembly of two segments representing C1-C 9 and C10-C21 of the structure. The C 1-C9 fragment was prepared by elaboration of commercially available (2R)-3-hydroxy-2-methylpropanoate at both ends of the three-carbon unit. Introduction of carbons 1-4 containing the gem-dimethyl unit was achieved in a convergent manner using a diastereoselective addition of a stannane equivalent of a β-keto ester dianion. An enantioselective addition of such a stannane equivalent for a β-keto ester dianion was also used to fashion one version of the C10-C21 subunit; however, the fragment assembly (using bimolecular esterification followed by ring-closing metathesis) with this subunit failed. Therefore, fragment assembly was achieved using a Wittig reaction; this was followed by macrolactonization to close the macrocycle. The C10-C21 subunit needed for this approach was prepared in an efficient manner using the Corey-Kim reaction as a key element. Other key reactions in the synthesis include a stereoselective SmI 2 reduction of a β-hydroxy ketone and a critical opening of a valerolactone with aniline which required extensive investigation.
Keck, Gary E.,Giles, Robert L.,Cee, Victor J.,Wager, Carrie A.,Yu, Tao,Kraft, Matthew B.
supporting information; experimental part
p. 9675 - 9691
(2009/04/07)

Total syntheses of epothilones B and D
A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12-C13, Wadsworth-Emmons olefination of methyl ketone 28 with the phosphonate ester 8, diastereoselective aldol condensation of aldehyde 5 with the enolate of keto acid derivatives to form the C6-C7 bond, selective deprotection of acid 52, and macrolactonization.
Jung, Jae-Chul,Kache, Rajashaker,Vines, Kimberly K.,Zheng, Yan-Song,Bijoy, Panicker,Valluri, Muralikrishna,Avery, Mitchell A.
p. 9269 - 9284
(2007/10/03)

Discovery of (E)-9,10-dehydroepothilones through chemical synthesis: On the emergence of 26-trifluoro-(E)-9,10-dehydro-12,13-desoxyepothilone B as a promising anticancer drug candidate
We provide a full account of the discovery of the (E)-9,10-dehydro derivatives of 12,13-desoxyepothilone B (dEpoB), a new class of antitumor agents with promising in vivo preclinical properties. The compounds, which are to date not available by modification of any of the naturally occurring epothilones, were discovered through total chemical synthesis. We describe how our investigations of ring-closing metathesis reactions in epothilone settings led to the first and second generation syntheses of (E)-9,10-dehydro-12,13- desoxyepothilone congeners. With further modifications, the synthesis was applied to reach a 26-trifluoro derivative compound (see compound 7). To conduct such studies and in anticipation of future development needs, the total synthesis which led to the initial discovery of compound 7 was simplified significantly. The total synthesis methodology used to reach compound 7 was then applied to reach more readily formulated compounds, bearing hydroxy and amino functionality on the 21-position (see compounds 45,62, and 63). Following extensive in vitro evaluations of these new congeners, compound 7 was nominated for in vivo evaluations in xenograft models. The data provided herein demonstrate a promising therapeutic efficacy, activity against large tumors, nonrelapseability, and oral activity. These results have identified compound 7 as a particularly promising compound for clinical development. The excellent, totally synthetic, route to 7 makes such a program quite feasible.
Rivkin, Alexey,Yoshimura, Fumihiko,Gabarda, Ana E.,Cho, Young Shin,Chou, Ting-Chao,Dong, Huajin,Danishefsky, Samuel J.
p. 10913 - 10922
(2007/10/03)

SYNTHESIS OF EPOTHILONES, INTERMEDIATES THERETO, ANALOGUES AND USES THEREOF
The present invention provides compounds of formula (I): as described generally and in classes and subclasses herein. The present invention additionally provides pharmaceutical compositions comprising compounds of formula (I) and provides methods of treating cancer comprising administering a compound of formula (I).
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Page 83

(2008/06/13)

Synthesis of epothilones B and D from D-glucose
An enantiospecific total synthesis of epothilones B and D from D-glucose is reported.
Ermolenko, Mikhail S,Potier, Pierre
p. 2895 - 2898
(2007/10/03)

Synthesis of epothilones, intermediates thereto, analogues and uses thereof
The present invention provides convergent processes for preparing epothilone A and B, desoxyepothilones A and B, and analogues thereof. Also provided are analogues related to epothilone A and B and intermediates useful for preparing same. The present invention further provides novel compositions based on analogues of the epothilones and methods for the treatment of cancer and cancer which has developed a multidrug-resistant phenotype.
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Page column 41

(2010/01/31)

Stereoselective total synthesis of epothilones by the metathesis approach involving C9-C10 bond formation
A stereoselective synthesis of epothilone B was achieved by the metathesis of the diene 1, by use of a new Grubbs catalyst to form the C9-C10 bond, followed by hydrogenation and deprotection of 2; TBS = tert-butyldimethylsilyl.
Sun, Jian,Sinha, Subhash C.
p. 1381 - 1383
(2007/10/03)

Total synthesis of epothilones B and D
(Matrix presented) A highly convergent total synthesis of the natural products epothilone B and D is described. The route is highlighted by efficient generation of a C12-C13 trisubstituted olefin which exploits a sequential Nozaki-Hiyama-Kishi coupling and a stereoselective thionyl chloride rearrangement.
Taylor, Richard E.,Chen, Yue
p. 2221 - 2223
(2007/10/03)

Total syntheses of epothilones B and D: Applications of allylstannanes in organic synthesis
Following exploratory studies which culminated in syntheses of the alcohol 16, a total synthesis of epothilones B and D is reported in which the trisubstituted 12,13-double-bond is introduced stereoselectively using the tin(IV) bromide-promoted reaction between the allylstannane 22 and the aldehyde 17. A Barton deoxygenation then gave the C(7)-C(15) fragment 25. After development of the thiazole containing side-chain, an aldol condensation with the ethyl ketone 36 gave the adduct 37 which was taken through to epothilone D 2 and then to epothilone B 1.
Martin, Nathaniel,Thomas, Eric J
p. 8373 - 8377
(2007/10/03)

The 12,13-diol cyclization approach for a truly stereocontrolled total synthesis of epothilone B and the synthesis of a conformationally restrained analogue
A highly convergent and stereocontrolled synthesis of epothilone B (1) has been developed. The epoxide moiety in 1 was generated by regioselective mesylation and base treatment of the 12,13-diol 30 which was formed by a chelate Cram controlled Grignard addition of 14 and methyl ketone 13. Both fragments were synthesized from the chiral carbon pool precursors (S)-citronellol and (S)-lactic acid, respectively. A highly diastereoselective aldol additon of epoxy-aldehyde 7 and the known Southern hemisphere ketone 8 delivered the full carbon skeleton, containing all the stereogenic centers of 1. Functional group manipulation, macrolactonization and removal of two protecting groups then yielded 1. The spatial closeness of the C4-β-methyl and C6-methyl group in the crystal structure of 1 inspired us to connect them through a methylene bridge to give a cyclohexanone derivative. Thus, the Northern hemisphere aldehyde 7 was added to the enolate of the cyclohexanone 47. Further manipulations and macrolactonization delivered the conformationally restrained epothilone derivative 42.
Martin, Harry J.,Pojarliev, Peter,Kaehlig, Hanspeter,Mulzer, Johann
p. 2261 - 2271
(2007/10/03)

Total synthesis of epothilone B, epothilone D, and cis- and trans-9,10-dehydroepothilone D
The phosphonium salt 35, representing one of the two principal subunits of the epothilones, was prepared from propargyl alcohol via heptenone 22. A Wittig reaction of the phosphorane from 35 with aldehyde 33, obtained from aldol condensation of ketone 27 with aldehyde 28, afforded 37. Seco acid 42 derived from 37 underwent lactonization to give cis-9,10-dehydroepothilone D (43) which was selectively reduced with diimide to yield epothilone D (4) and, after epoxidation, epothilone B (2). An alternative route to epothilone D employed alkyne 39, obtained from 33, in a Castro-Stephens reaction with allylic bromide 34 to furnish enyne 40. The latter was semi-hydrogenated to provide 37. Alkyne 46, prepared from alcohol 45, was converted to trans-vinylstannane 47 which, in a Stille coupling with allylic chloride 50, gave 51. Seco acid 52 derived from 51 underwent lactonization to give trans-9,10-dehydroepothilone D (54). Bioassay data comparing the antiproliferative activity and tubulin polymerization of 43 and 54 with epothilone B (2), epothilone D (4), and paclitaxel (7) showed that the synthetic analogues were less potent than their natural counterparts, although both retain full antiproliferative activity against a paclitaxel-resistant cell line. No significant difference in potency was noted between cis analogue 43 and its trans isomer 54.
White,Carter,Sundermann,Wartmann
p. 5407 - 5413
(2007/10/03)

Total Syntheses of Epothilones B and D
Total syntheses of the microtubule stabilizing antitumor drugs epothilone B and D are described, starting from optically pure (S)-malic acid and methyl (R)-3-hydroxy-2-methylpropionate. The synthesis is highly convergent by coupling the three fragments C1-C6 (fragment D), C7-C10 (fragment C), and C11-C21 (fragment B). Key steps are two stereoselective Wittig type olefinations to generate the 12,13- and 16,17-double bonds, an enantioselective Mukaiyama aldol addition to synthesize fragment D, and a sulfone anion allyl iodide alkylation to connect fragments B and C. Finally fragment D was attached to the B + C fragment via aldol addition.
Mulzer, Johann,Mantoulidis, Andreas,Oehler, Elisabeth
p. 7456 - 7467
(2007/10/03)

How stable are epoxides? A novel synthesis of epothilone B
Remarkable stability of the oxirane function is displayed over a number of synthetic operations in a novel synthesis of the antitumor compound epothilone B. The cis-epoxide, generated very early by dihydroxylation of an (E)-olefin, was resistant to more than ten synthetic steps under a wide variety of reaction conditions. TBS = tert-butyldimethylsilyl.
Martin, Harry J.,Drescher, Martina,Mulzer, Johann
p. 581 - 583
(2007/10/03)

Enantioselective total synthesis of epothilones A and B using multifunctional asymmetric catalysis
An enantioselective total synthesis of epothilones A (1) and B (2) using multifunctional asymmetric catalysis such as a cyanosilylation of an aldehyde, an aldol reaction of an unmodified ketone with an aldehyde, and a protonation in the conjugate addition of a thiol to an α,β-unsaturated thioester has been achieved. We divided 1 and 2 into fragment A, fragment B, and fragment C. A catalytic asymmetric synthesis of fragments A and B was accomplished using a catalytic asymmetric cyanosilylation as a key step. An enantiocontrolled synthesis of fragment C was achieved in two ways. One is the use of a direct catalytic asymmetric aldol reaction of an unmodified ketone with an aldehyde as a key step, and the other utilizes a catalytic asymmetric protonation in the conjugate addition of a thiol to an α,β-unsaturated thioester as a key step. Suzuki cross-coupling of fragment A with fragment C followed by Yamaguchi lactonization as key steps led to an enantiocontrolled synthesis of epothilone A (1). On the other hand, Suzuki cross-coupling of fragment B with fragment C followed by Yamaguchi lactonization accomplished an enantiocontrolled synthesis of epothilone B (2).
Sawada, Daisuke,Kanai, Motomu,Shibasaki, Masakatsu
p. 10521 - 10532
(2007/10/03)

Epothilone B and its derivatives as novel antitumor drugs: Total and partial synthesis and biological evaluation
Microtubule stabilizing natural products, as exemplified by paclitaxel (taxolR), are being considered as novel drugs against malignant therapy resistent solid tumors. Among these compounds, epothilone B and some of its derivatives have emerged as particularly promising candidates for industrial development. The total and partial syntheses of these compounds are described in detail, and some of the most important recent results on their biological activity are discussed.
Mulzer, Johann
p. 205 - 238
(2007/10/03)

Synthesis of 16-desmethylepothilone B: Improved methodology for the rapid, highly selective and convergent construction of epothilone B and analogues
During a synthesis of 16-desmethylepothilone B new methods for the convergent and highly stereoselective synthesis of epothilone B and analogues were developed.
Nicolaou,Hepworth, David,Finlay, M. Ray V.,King, N. Paul,Werschkun, Barbara,Bigot, Antony
p. 519 - 520
(2007/10/03)

New chemical synthesis of the promising cancer chemotherapeutic agent 12,13-desoxyepothilone B: Discovery of a surprising long-range effect on the diastereoselectivity of an aldol condensation
The epothilones are naturally occurring cytotoxic molecules that possess the remarkable ability to arrest cell division through the stabilization of microtubule assemblies. Our in vivo studies with 12,13-desoxyepothilone B (dEpoB), have established that the desoxy compound is well tolerated and virtually curative against a variety of sensitive and resistant xenograft tumors in animal models. In light of these discoveries, we sought a chemical synthesis of dEpoB that would be able to support a serious and substantial discovery research program directed toward the clinical development of this molecule. The overall strategy for this endeavor assumed the ability to synthesize dEpoB from three constructs which include an achiral β,δ-diketo ester construct A, an (S)-2-methylpentenal moiety B, and the thiazoyl-containing vinyl iodide moiety C. We envisioned that a diastereoselective aldol condensation between an achiral C5-C6 (Z)-metalloenolate derived from construct A and an (S)-2-methylalkanal fragment, B, would generate the desired C6-C7 bond. Second, a B-alkyl Suzuki coupling between the vinyl iodide construct C and an alkyl borane would form the C11-C12 bond. Finally, a late-stage reduction of the C3 ketone to the requisite C3 alcohol with high asymmetric induction would permit us to introduce the β,δ-diketo ester fragment A, into the synthesis as a readily accessible achiral building block. The governing concepts for our new synthesis are described herein.
Harris, Christina R.,Kuduk, Scott D.,Balog, Aaron,Savin, Ken,Glunz, Peter W.,Danishefsky, Samuel J.
p. 7050 - 7062
(2007/10/03)

A highly stereoselective synthesis of epothilone B
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White, James D.,Carter, Rich G.,Sundermann, Kurt F.
p. 684 - 685
(2007/10/03)

Total synthesis of (-)-epothilone B
The sixteen-membered ring macrolide (-)-epothilone B 1 has been synthesized by a route which features stereospecific methylation of an (E)-γ,δ-epoxy acrylate, the use of a double asymmetric reaction employing (R,R)-diisopropyltartrate and (E)-crotylboronate, and ring closure by means of an olefin metathesis reaction.
May, Scott A.,Grieco, Paul A.
p. 1597 - 1598
(2007/10/03)

Total syntheses of epothilones A and B via a macrolactonization-based strategy
The total syntheses of epothilones A (1) and B (2) and several analogues thereof are described. The reported strategy relies on a macrolactonization approach and features selective epoxidation of the macrocycle double bond in precursors 3 and 4 (Scheme 1), respectively, as well as high convergency and flexibility. Building blocks 9-12 and 15 were constructed by asymmetric processes and coupled via Wittig, aldol, and macrolactonization reactions to afford the basic skeleton of epothilones and that of several of their analogues by a relatively short route. The utilization ofintermediate 14, obtained via a stereoselective Wittig reaction and its Enders coupling to SAMP hydrazone 13 (Scheme 8), in combination with a stereoselective aldol reaction with the modified substrate 69 (Scheme 10) improved the stereoselectivity and efficiency of the total synthesis of these new and highly potent microtubule binding antitumor agents.
Nicolaou,Ninkovic,Sarabia,Vourloumis,He,Vallberg,Finlay,Yang
p. 7974 - 7991
(2007/10/03)

Total Synthesis of ( - )-Epothlone B: An Extension of the Suzuki Coupling Method and Insights into Structure - Activity Relationships of the Epothilones
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Su, Dai-Shi,Meng, Dongfang,Bertinato, Peter,Balog, Aaron,Sorensen, Erik J.,Danishefsky, Samuel J.,Zheng, Yu-Huang,Chou, Ting-Chao,He, Lifeng,Horwitz, Susan B.
p. 757 - 759
(2007/10/03)

Total Synthesis of Epothilones A and B
Convergent, stereocontrolled total syntheses of the microtubule-stabilizing macrolides epothilones A (2) and B (3) have been achieved. Four distinct ring-forming strategies were pursued (see Scheme 1). Of these four, three were reduced to practice. In one approach, the action of a base on a substance possessing an acetate ester and a nonenolazable aldehyde brought about a remarkably effective macroaldolization see (89 -> 90 + 91; 99 -> 100 + 101), simultaneously creating the C2-C3 bond and the hydroxyl-bearing stereocenter at C-3. Alternatively, the 16-membered macrolide of the epothilones could be fashioned through a C12-C13 ring-closing olefin metathesis (e.g. see 111 -> 90 + 117; 122 -> 105 + 123) and through macrolactonization of the appropriate hydroxy acid (e.g. see 88 -> 93). The application of a stereospecific B-alkyl Suzuki coupling strategy permitted the establishment of a cis-C12-C13 olefin, thus setting the stage for an eventual site- and diastereoselective epoxidation reaction (see 96 -> 2; 106 -> 3). The development of a novel cyclopropane solvolysis strategy for incorporating the geminal methyl groups of the epothilones (see 39 -> 40 -> 41), and the use of Lewis acid catalyzed diene-aldehyde cyclocondensation (LACDAC) (see 35 + 36 -> 37) and asymmetric allylation (see 10 -> 76) methodology are also noteworthy.
Dongfang, Meng,Bertinato, Peter,Balog, Aaron,Su, Dai-Shi,Kamenecka, Ted,et al.
p. 10073 - 10092
(2007/10/03)

Chemical Properties

Appearance/Colour :white powder
Melting Point: 95-97 °C
Boiling Point: 680.188 °C at 760 mmHg
Flash Point:365.165 °C
Density: 1.137 g/cm³
Solubility:Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 35 mg/ml).
Storage Temp.:Store at -20°C
Vapor Pressure: 0mmHg at 25°C
Refractive Index: 1.532
PKA: 13.57±0.70(Predicted)
PSA: 137.49000
LogP: 4.47750

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Zhuozhou Wenxi import and Export Co., Ltd
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HANWAYS CHEMPHARM CO.,LIMITED
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Shanghai Upbio Tech Co.,Ltd
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Xi'an Faithful Biotech Co., Ltd.
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Baoji Guokang Healthchem co.,ltd
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Qingdao Beluga Import and Export Co., LTD
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Shandong Hanjiang Chemical Co., Ltd.
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Changchun Artel lmport and Export trade company
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Hubei Jiutian Bio-medical Technology Co., Ltd
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Hebei Quanhe Biotechnology Co. LTD
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Henan Wentao Chemical Product Co., Ltd.
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Article Database

152044-54-7

Articles about 152044-54-7Total 32 be found

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Chemical Properties

Appearance/Colour :white powder

Melting Point: 95-97 °C

Boiling Point: 680.188 °C at 760 mmHg

Flash Point:365.165 °C

Density: 1.137 g/cm³

Solubility:Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 35 mg/ml).

Storage Temp.:Store at -20°C

Vapor Pressure: 0mmHg at 25°C

Refractive Index: 1.532

PKA: 13.57±0.70(Predicted)

PSA: 137.49000

LogP: 4.47750

Global suppliers and manufacturers of 152044-54-7total 129 suppliers on LookChem

Article Database

152044-54-7

Articles about 152044-54-7Total 32 be found

More Articles about upstream products of 152044-54-7

More Articles about downstream products of 152044-54-7

Chemical Properties

Appearance/Colour :white powder

Melting Point: 95-97 °C

Boiling Point: 680.188 °C at 760 mmHg

Flash Point:365.165 °C

Density: 1.137 g/cm3

Solubility:Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 35 mg/ml).

Storage Temp.:Store at -20°C

Vapor Pressure: 0mmHg at 25°C

Refractive Index: 1.532

PKA: 13.57±0.70(Predicted)

PSA: 137.49000

LogP: 4.47750

Global suppliers and manufacturers of 152044-54-7total 129 suppliers on LookChem

Density: 1.137 g/cm³