- The electrophilic cleavage of cyclopropylcarbinylstannanes. Confirmation of Traylor's prediction
-
The reaction of cyclopropylcarbinyltrialkylstannanes (CPCSnR3) 1a (R = Me) and 1b (R = Bu) with sulfur dioxide in chloroform or methanol yields the homoallylic tin sulphinates 2a and 2b respectively. The reaction of 1a with iodine in chloroform yields predominantly 4-iodo-1-butene (3) and trimethyltin iodide while in methanol the corresponding reaction yields CPCSnMe2I (4) and methyl iodide.
- Lucke,Young
-
-
Read Online
- Synthesis of Low-Viscosity Ionic Liquids for Application in Dye-Sensitized Solar Cells
-
Two types of ionic liquids (ILs), 1-(3-hexenyl)-3-methyl imidazolium iodide and 1-(3-butenyl)-3-methyl imidazolium iodide, are synthesized by introducing an unsaturated bond into the side alkyl chain of the imidazolium cation. These new ionic liquids exhibit high thermal stability and low viscosity (104 cP and 80 cP, respectively). The molecular dynamics simulation shows that the double bond introduced in the alkane chain greatly changes the molecular system space arrangement and diminishes the packing efficiency, leading to low viscosity. The low viscosity of the synthesized ionic liquids would enhance the diffusion of redox couples. This enhancement is detected by fabricating dye-sensitized solar cells (DSSCs) with electrolytes containing the two ILs and I2. The highest efficiency of DSSCs is 6.85 % for 1-(3-hexenyl)-3-methyl imidazolium iodide and 5.93 % for 1-(3-butenyl)-3-methyl imidazolium iodide electrolyte, which is much higher than that of 5.17 % with the counterpart 1-hexyl-3-methyl imidazolium iodide electrolyte.
- Fang, Yanyan,Ma, Pin,Cheng, Hongbo,Tan, Guoyu,Wu, Jiaxin,Zheng, Jiaxin,Zhou, Xiaowen,Fang, Shibi,Dai, Yuhua,Lin, Yuan
-
-
Read Online
- Cobalt-Catalyzed Regioselective Olefin Isomerization under Kinetic Control
-
Olefin isomerization is a significant transformation in organic synthesis, which provides a convenient synthetic route for internal olefins and remote functionalization processes. The selectivity of an olefin isomerization process is often thermodynamically controlled. Thus, to achieve selectivity under kinetic control is very challenging. Herein, we report a novel cobalt-catalyzed regioselective olefin isomerization reaction. By taking the advantage of fine-tunable NNP-pincer ligand structures, this catalytic system features high kinetic control of regioselectivity. This mild catalytic system enables the isomerization of 1,1-disubstituted olefins bearing a wide range of functional groups in excellent yields and regioselectivity. The synthetic utility of this transformation was highlighted by the highly selective preparation of a key intermediate for the total synthesis of minfiensine. Moreover, a new strategy was developed to realize the selective monoisomerization of 1-alkenes to 2-alkenes dictated by installing substituents on the γ-position of the double bonds. Mechanistic studies supported that the in situ generated Co-H species underwent migratory insertion of double bond/β-H elimination sequence to afford the isomerization product. The less hindered olefin products were always preferred in this cobalt-catalyzed olefin isomerization due to an effective ligand control of the regioselectivity for the β-H elimination step.
- Liu, Xufang,Zhang, Wei,Wang, Yujie,Zhang, Ze-Xin,Jiao, Lei,Liu, Qiang
-
supporting information
p. 6873 - 6882
(2018/05/30)
-
- Synthetic studies toward the brasilinolides: Controlled assembly of a protected C1-C38 polyol based on fragment union by complex aldol reactions
-
The brasilinolides are an architecturally complex family of 32-membered macrolides, characterised by potent immunosuppressant and antifungal properties, which represent challenging synthetic targets. By adopting a highly convergent strategy, a range of asymmetric aldol/reduction sequences and catalytic protocols were employed to assemble a series of increasingly elaborate fragments. The controlled preparation of suitable C1-C19 and C20-C38 acyclic fragments 5 and 6, containing seven and 12 stereocentres respectively, was first achieved. An adventurous C19-C20 fragment union was then explored to construct the entire carbon chain of the brasilinolides. This pivotal coupling step could be performed in a complex boron-mediated aldol reaction to install the required C19 hydroxyl stereocentre when alternative Mukaiyama-type aldol protocols proved unrewarding. A protected C1-C38 polyol 93 was subsequently prepared, setting the stage for future late-stage diversification toward the various brasilinolide congeners. Throughout this work, asymmetric boron-mediated aldol reactions of chiral ketones with aldehydes proved effective both for controlled fragment assembly and coupling with predictable stereoinduction from the enolate component.
- Paterson, Ian,Housden, Michael P.,Cordier, Christopher J.,Burton, Paul M.,Mühlthau, Friedrich A.,Loiseleur, Olivier
-
supporting information
p. 5716 - 5733
(2015/05/27)
-
- Direct Generation of Triketide Stereopolyads via Merged Redox-Construction Events: Total Synthesis of (+)-Zincophorin Methyl Ester
-
(+)-Zincophorin methyl ester is prepared in 13 steps (longest linear sequence). A bidirectional redox-triggered double anti-crotylation of 2-methyl-1,3-propane diol directly assembles the triketide stereopolyad spanning C4-C12, significantly enhancing step economy and enabling construction of (+)-zincophorin methyl ester in nearly half the steps previously required.
- Kasun, Zachary A.,Gao, Xin,Lipinski, Radoslaw M.,Krische, Michael J.
-
supporting information
p. 8900 - 8903
(2015/08/03)
-
- Chemoenzymatic asymmetric total synthesis of nonanolide (Z)-cytospolides D, E and their stereoisomers
-
Chemoenzymatic asymmetric total synthesis of the (Z)-isomer of the naturally occurring decanolide cytospolides D, E and six stereoisomers is reported. The main highlight of the synthetic venture involves ring-closing metathesis (RCM) reaction of a suitably functionalized ester compound, which was assembled by the Yamaguchi coupling of the required acid and alcohol fragments. The alcohol fragment was ac- cessed by two alternative chemoenzymatic processes, one being hydroxynitrile lyase mediated hydrocyanation, whereas lipase-catalyzed transesterification was the key sep in the second route. The acid fragment was constructed by an enantioselective enzymatic desymmetrization (EED) of prochiral 2-methyl-1,3-propanediol and Corey-Bakshi-Shibata (CBS) mediated stereoselective carbonyl reduction.
- Rej, Rohan Kalyan,Nanda, Samik
-
p. 860 - 871
(2014/03/21)
-
- Chemoenzymatic Asymmetric Total Synthesis of Nonanolide (Z)-Cytospolides D, e and Their Stereoisomers
-
Chemoenzymatic asymmetric total synthesis of the (Z)-isomer of the naturally occurring decanolide cytospolides D, E and six stereoisomers is reported. The main highlight of the synthetic venture involves ring-closing metathesis (RCM) reaction of a suitably functionalized ester compound, which was assembled by the Yamaguchi coupling of the required acid and alcohol fragments. The alcohol fragment was accessed by two alternative chemoenzymatic processes, one being hydroxynitrile lyase mediated hydrocyanation, whereas lipase-catalyzed transesterification was the key sep in the second route. The acid fragment was constructed by an enantioselective enzymatic desymmetrization (EED) of prochiral 2-methyl-1,3-propanediol and Corey-Bakshi-Shibata (CBS) mediated stereoselective carbonyl reduction.
- Rej, Rohan Kalyan,Nanda, Samik
-
p. 860 - 871
(2015/10/05)
-
- Enantiospecific intramolecular heck reactions of secondary benzylic ethers
-
Enantioenriched methylenecyclopentanes are synthesized by stereospecific, nickel-catalyzed Heck cyclizations of secondary benzylic ethers. The reaction proceeds in high yield and enantiospecificity for benzylic ethers of both π-extended and simple arenes. Ethers with pendant 1,2-disubstituted olefins form trisubstituted olefins with control of both absolute configuration and alkene geometry. Diastereoselective synthesis of a polycyclic furan is demonstrated.
- Harris, Michael R.,Konev, Mikhail O.,Jarvo, Elizabeth R.
-
supporting information
p. 7825 - 7828
(2014/06/23)
-
- Skeletal and stereochemical diversification of tricyclic frameworks inspired by Ca2+-ATPaSe inhibitors, artemisinin and transtaganolide D
-
(Chemical Equation Presented) Inspired by the common skeletal motifs of Ca2+-ATPases inhibitors involving artemisinin and transtaganolide D, small molecule collections with the three-dimensional structural diversity of tricyclic systems were designed and expeditiously synthesized (4-5 steps). A synthetic strategy featuring stereochemical diversification of ring-junctions and control of cyclizatlon modes was devised to access varied molecular architectures in a systematic fashion.
- Oguri, Hiroki,Yamagishi, Yutaka,Hiruma, Takahisa,Oikawa, Hideaki
-
supporting information; experimental part
p. 601 - 604
(2009/09/25)
-
- Synthetic studies toward jatrophane diterpenes from Euphorbia characias. enantioselective synthesis of (-)-15-O-Acetyl-3-O-propionyl-17-norcharaciol
-
The enantioselective synthesis of (+)-17-norcharaciol is described. An uncatalyzed intramolecular carbonyl-ene reaction and a ring-closing metathesis were used as key C/C-connecting transformations to assemble the trans-bicyclo[10.3.0]pentadecane norditerpenoid core. We also report the evolution of our synthetic strategy toward the fully substituted characiol skeleton and the experiences from this venture.
- Helmboldt, Hannes,Hiersemann, Martin
-
scheme or table
p. 1698 - 1708
(2009/10/02)
-
- CGRP Receptor Antagonists
-
The disclosure generally relates to the novel compounds of formula I, including their salts, which are CGRP receptor antagonists. The disclosure also relates to pharmaceutical compositions and methods for using the compounds in the treatment of CGRP related disorders including migraine and other headaches, neurogenic vasodilation, neurogenic inflammation, thermal injury, circulatory shock, flushing associated with menopause, airway inflammatory diseases such as asthma, and chronic obstructive pulmonary disease (COPD).
- -
-
Page/Page column 19
(2009/10/21)
-
- Asymmetric synthesis of terminal N-tert-butylsulfinyl aziridines from organoceriums and an α-chloroimine
-
(Chemical Equation Presented) Addition of N-(2-chloroethylidene)-tert- butylsulfinamide to organocerium reagents in DMPU/THF (1:10) at -78°C followed by warming to 25°C provides terminal N-tert-butylsulfinyl aziridines in good yields (63-92%, nine examples) and diastereomeric ratios (85:15->99:1).
- Hodgson, David M.,Kloesges, Johannes,Evans, Brian
-
supporting information; experimental part
p. 2781 - 2783
(2009/05/30)
-
- Regioselective oxidative cation-olefin cyclization of poly-enes: Catalyst turnover via hydride abstraction
-
Electrophilic P2Pt2+ complexes are shown to catalyze the regio- and diastereoselective oxidative cascade cyclization of poly-enes. The reactions are stereospecific with respect to the initiating alkenes geometry and suggest an all-chair, semiconcerted transition structure. Catalyst turnover after cyclization apparently occurs via β-hydride elimination and subsequent hydride abstraction (from P2Pt-H+) by added Trityl cation (in the form of trityl methyl ether or a resin version thereof) to regenerate the active P2Pt2+ state. One intriguing possibility is that the high regioselectivity observed in the β-H elimination is due to a regio-defining β-agostic resting state. Copyright
- Mullen, Charles A.,Gagne, Michel R.
-
p. 11880 - 11881
(2008/03/30)
-
- Synthesis of the norjatrophane diterpene (-)-15-acetyl-3-propionyl-17- norcharaciol
-
A scalable enantioselective synthesis of the nonnatural 17-norjatrophane diterpene 3-propionyl-15-acetyl-17-norcharaciol is described. Key C/C-connecting transformations are an Evans aldol reaction, an intramolecular carbonyl ene reaction, a Horner-Wadsworth-Emmons olefination, and a ring-closing metathesis for the formation of a 12-membered carbacycle.
- Helmboldt, Hannes,Koehler, Daniel,Hiersemann, Martin
-
p. 1573 - 1576
(2007/10/03)
-
- Electrophilic cleavage of cyclopropylmethystannanes: An experimental comparison of σ-σ and σ-π conjugation
-
(Chemical Equation Presented) Cyclopropylmethyltrimethylstannanes undergo electrophilic cyclopropane cleavage in chloroform with simple inorganic electrophiles (H+, SO2, I2) in a homologous reaction to the SE′ cleavage of allylic stannanes. The σ-σ conjugation between the carbon-tin bond and cyclopropane orbitals observed spectroscopically in the parent cyclopropylmethyltrimethylstannane is responsible for a rate enhancement of ca. 102 toward iodinolysis, relative to comparable alkyl stannanes. This acceleration is considerably less, however, than the ca. 109-fold rate enhancement provided by the corresponding σ-π conjugation in allylic stannanes. Methanol-tin coordination appears to reduce the activating influence of the metal, promoting methyl cleavage over cyclopropane fission with acid and iodine. Decreased σ-σ conjugation can also explain the decreased reactivity of cyclopropyltriphenylstannane compared with its trimethyltin counterpart. Cyclopropylmethylstannanes do not undergo the synthetically useful addition of aldehydes under conditions that facilitate the corresponding reaction of allylic stannanes.
- Lucke, Andrew J.,Young, David J.
-
p. 3579 - 3583
(2007/10/03)
-
- The Use of Butane Diacetals of Glycolic Acid as Precursors for the Synthesis of the Phytotoxic Calmodulin Inhibitor Herbarumin II
-
The total synthesis of phytotoxic nonenolide herbarumin II (1) has been achieved by implementation of butane diacetal (BDA)-desymmetrised glycolate building blocks. Three of the four stereogenic centres present in the key coupling fragments were generated from both enantiomeric forms of the BDA building block in highly diastereoselective alkylation and aldol reactions.
- Diez, Elena,Dixon, Darren J.,Ley, Steven V.,Polara, Alessandra,Rodriguez, Felix
-
p. 3717 - 3729
(2007/10/03)
-
- Photocycloisomerization of Boc-protected 5-alkenyl-2,5-dihydro-1H-pyrrol-2-ones
-
On irradiation (254 nm), the newly synthesized Boc-protected 5-alkenyl-2,5-dihydro-1H-pyrrol-2-ones 13 undergo regioselective intramolecular [2 + 2] photocycloadditions. While the allyl derivatives 13a-13c afford mainly azatricyclo[3.3.0.02.7]octanones, i.e., crossed cycloadducts, the butenyl- and pentenyl-substituted compounds 13d and 13e isomerize preferentially to straight cycloadducts.
- Wrobel, Matthias N.,Margaretha, Paul
-
p. 515 - 521
(2007/10/03)
-
- From amino acids to fused chiral pyrrolidines and piperidines via the INOC route
-
Intramolecular nitrile oxide olefin cycloaddition (INOC) reactions of oximes 1-3 and of 24-27 derived from 1-amino acids have been found to proceed stereoselectively, yielding tricyclic fused pyrrolidines and piperidines. Further manipulation led to chiral hydroxymethyl-substituted fused piperidines 33-35 and to 3-amino-4-(1-hydroxypropyl)-2-mercaptomethyl-N- methylpiperidine (36). The structures and stereochemistries of the fused systems, as well as those of the piperidines, have been established by NMR.
- Falb, Eliezer,Nudelman, Abraham,Gottlieb, Hugo E.,Hassner, Alfred
-
p. 645 - 655
(2007/10/03)
-
- Synthesis of enantiomerically pure (2R,5S)- and (2R,5R)-5-hydroxypipecolic acid from glycinate Schiff bases
-
An asymmetric synthesis of cis- and trans-5-hydroxy-(D)-pipecolic acid, starting from glycinate Schiff bases is described. The approach involves the stereoselective alkylation to generate an unsaturated side chain which on cyclisation leads to the desired trans- or cis-5-hydroxy-(D)-pipecolic acid.
- Hoarau, Sylvie,Fauchere, Jean Luc,Pappalardo, Louis,Roumestant, Marie Louise,Viallefont, Philippe
-
p. 2585 - 2593
(2007/10/03)
-
- Regiochemical and Stereochemical Studies on Halocyclization Reactions of Unsaturated Sulfides
-
The regiochemistry and stereochemistry for the halocyclization reactions of unsaturated benzyl sulfides have been examined as a function of tether length, type of unsaturation (carbon-carbon double bond versus carbon-carbon triple bond), substituents, and halogenating agent.Alkenyl sulfides were found to react with iodine or bromine at room temperature to give five-membered ring cycloadducts exclusively over those having four-membered rings, while for larger systems, six-membered ring products are formed preferentially over their five-membered ring isomers and exclusively over the seven-membered ring adducts.The endo- versus exo-regioselectivity of these alkenyl sulfide ring closure most likely reflects the difference in thermodynamic stabilities of the β-halo sulfide cycloadducts, which are able to equilibrate via a common episulfonium intermediate.The efficiency of cyclization process markedly drops off for these alkenyl sulfides as the tether length increases beyond four intervening carbon centers.Thus, while the halogenations of 3-butenyl sulfides and 4-pentenyl sulfides give high yields of cycloadducts, those of 5-hexenyl sulfides afford only small amounts of cyclized products and large quantities of acyclic dibromides.Conversely, the reactions of acetylenic sulfides with iodine give uniformly high yields and regiochemical control regardless of the tether length.Thus, 3-butynyl and 4-pentynyl sulfides cyclize cleanly to the five-membered ring while 5-hexynyl sulfides give exclusively the six-membered ring.The products arising from these alkynyl sulfide ring closures are believed to be formed under kinetic control.The methodology has been applied to the synthesis of unusual bicyclic β-lactams related to the penicillin family of antibiotics.
- Ren, Xiao-Feng,Turos, Edward,Lake, Charles H.,Churchill, Melvyn Rowen
-
p. 6468 - 6483
(2007/10/03)
-
- A General Mechanistic Scheme for Intramolecular Electrochemical Hydrocyclizations. Mechanism of the Electroreductive Cyclization of ω-Keto-α,β-unsaturated Esters
-
A systematic procedure is suggested for formulating possible mechanisms by which electrochemical hydrocyclization and dehydrocyclization can occur.A combination of linear sweep voltammetry (LSV) and chemical and electrochemical arguments can be used to reduce the mechanistic possibilities to a small set or even a unique mechanism.The procedure is applied to the reductive cyclization of ω-keto-α,β-unsaturated esters.Of the several hundred mechanistic possibilities for this process, the combination of LSV and chemical arguments can reduce the list to four; preparative-scale electrolysis of a specially designed substrate permits assignment of a unique mechanism, the e-P-d-c-p path, at low concentrations of electroactive substance.
- Fry, Albert J.,Little, R. Daniel,Leonetti, Joseph
-
p. 5017 - 5026
(2007/10/02)
-
- Attempted synthesis of 1,3,5-triphenyl-2,4,9-trithia-1,3,5-triplumbaadamantane. Decomposition of organolead iodides
-
MNDO calculations suggest that the strength of the bridgehead carbon-hydrogen bond in 2,4,9-trithia-1,3,5-triplumbaadamantane (2a) should be only 54 kcal/mol and the hydride affinity of the corresponding bridgehead cation 2a+ should be only 215 kcal/mol. As a donor of hydrogen atoms or hydride, plumbaadamantane 2a should therefore be even more reactive than the analogous stannaadamantane 1a. Unfortunately, substituted derivative 2b could not be prepared from (Ph3PbCH2)3CH by controlled iodinolysis followed by treatment of the intermediate hexaiodide (PhI2PbCH2)3CH with Ph3SnSSnPh3. This failure results in part from the tendency of organolead diiodides R2PbI2 to undergo redistribution reactions that produce unstable triiodides RPbI3. Diiodides capable of intramolecular redistributions are particularly reactive. The resulting triiodides then decompose by a formal reductive elimination of RI and PbI2. Since the iodinolysis of (cyclopropylmethyl)triphenylplumbane (11) yields mainly (iodomethyl)cyclopropane instead of ring-opened products derived from cyclopropylmethyl cations or radicals, we suggest that the reductive elimination of RI and PbI2 from RPbI3 is concerted.
- Kobayashi, Michio,Latour, Stéphan,Wuest, James D.
-
p. 2908 - 2913
(2008/10/08)
-
- One-pot, one- and multi-carbon homologation of alkyl halides; reaction of Grignard reagents with chloroiodomethane
-
Reaction of a Grignard reagent (RMgX) with chloroiodomethane affords the corresponding iodide (RI) and, depending on R, solvent and temperature, iodides which are one-carbon and multicarbon homologs of RX. Allyl iodide but not allyl bromide can be monohomologated by the combined action of chloroiodomethane and isopropyl Grignard.
- Hahn,Tompkins
-
p. 937 - 940
(2007/10/02)
-
- Radical Chain Mechanism for Alkyl Rearrangement in Organocobalt Complexes
-
The molecular rearrangement of a series of 5-hexenylcobalt(III) complexes of various Schiff bases is demonstrated to proceed via an unusual radical chain process.Thus the facility with the 5-hexenyl --> cyclopentylmethyl rearrangement occurs is highly dependent on the presence of trace impurities which can vary from the age of a highly purified sample to the presence of air.We find that the rearrangement of (5-hexenyl)CoIII(salen) I can be deliberately controlled by inhibiting it completely or by promoting it rapidly.For example, the addition of cobalt(II), nitroxide (TEMPO), dioxygen, or dihydroanthracene as well as an electrochemical preduction procedure can effectively squelch the 5-hexenyl rearrangement.Conversely, chemical and electrochemical oxidations with a ferrocenium salt and a platinium anode at 0.4 V, respectively, trigger the rearrangement.In each case, the limited molar amounts of additives (or faradays of charge) are sufficiently small to ensure high kinetic chain lenghts.Inhibition and initiation of the chain process by these techniques relate directly to the destruction and generation, respectively, of alkyl radicals as the prime reactive intermediates.Accordingly, a homolytic displacement (SH2) of the alkylcobalt(III) complex is proposed, in conjuction with the well-known rearrangement of the hexenyl radical, to constitute the two-step propagation cycle in Scheme III.Such a mechanism accounts for the intermolecular character of the hexenyl rearrangement as established by crossover experiments and the observation of a concurrent alkyl exchange which would otherwise be difficult to explain.The spontaneous rearrangement of a freshly prepared sample of (hexenyl)CoIII(salen) and the dichotomous effect of pyridine as a donor ligand are both readily accommodated within the content of the mechanism in Scheme III.
- Samsel, E. G.,Kochi, J. K.
-
p. 4790 - 4804
(2007/10/02)
-
- Vibrational Spectra and Conformations of (Iodomethyl)cyclopropane and Epiiodohydrin
-
The infrared (4000-400 cm-1) spectra of (iodomethyl)cyclopropane and epiiodohydrin in all three physical states have been recorded.The Raman (3500-50 cm-1) spectra of these two molecules in condensed phases have also been obtained.For (iodomethyl)cyclopropane no multiple Q branches were observed in the gase-phase infrared spectrum nor were any liquid-phase peaks observed to vanish upon crystallization.On the basis of these data and on the liquid-phase Raman depolarization ratios (which suggest that all observed Raman lines are polarized) it has been concluded that (iodomethyl)cyclopropane exists solely in the (nonsymmetric) gauche conformation in all states of matter.On the other hand, epiiodohydrin exhibits several gas-phase infrared band contours with "extra" Q branches and ten liquid-phase Raman conformer doublets, wherein one member of each doublet disappears when the annealed solid phase is obtained.These data have been interpreted in terms of a gauche-1 (70percent)/gauche-2 (30percent) conformational equilibrium for liquid epiiodohydrin at room temperature, with only the gauche-1 conformer remaining in the crystalline sample.From a variable-temperature (-74 to 25 deg C) study of the base-line-resolved liquid-phase Raman doublet at 940/914 cm-1, an enthalpy difference between conformers of 0.50 +/- 0.05 kcal/mol has been determined, with the gauche-1 conformer the more stable.No evidence for a cis conformation of either molecule was found, apparently as a result of strong steric interactions between the iodine atom and β-ring hydrogen atoms.For these molecules, vibrational assignments, which are in excellent agreement with the vibrational assignments of other (halomethyl)cyclopropanes and epihalohydrins, have also been proposed.
- Wurrey, C. J.,Yeh, Y. Y.,Krishnamoorthi, R.,Berry, R. J.,DeWitt, J. E.,Kalasinsky, V. F.
-
p. 4059 - 4063
(2007/10/02)
-
- Diphosphorus Tetraiodide. A Valuable Reagent in Cyclopropane Chemistry
-
The behaviour of P2I4 and PI3 towards cyclopropyl alcohols, cyclopropyl ketones, α-seleno ketones, and ozonides is reported.
- Denis, J. N.,Krief, Alain
-
p. 229 - 230
(2007/10/02)
-
- A Total Synthesis of (+/-)-Eremophilenolide
-
(+/-)-Eremophilenolide was synthesized in 18percent overall yield from cyclohexanone.The A/B-ring system was prepared via butenylcyclohexenol-annulation and the 2-furanone unit via α-epoxyketone-ynamine reaction.
- Pennanen, Seppo
-
p. 261 - 264
(2007/10/02)
-