- Design, Synthesis, and Activity Evaluation of Novel Acyclic Nucleosides as Potential Anticancer Agents in Vitro and in Vivo
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In the present work, 103 novel acyclic nucleosides were designed, synthesized, and evaluated for their anticancer activities in vitro and in vivo. The structure-activity relationship (SAR) studies revealed that most target compounds inhibited the growth of colon cancer cells in vitro, of which 3-(6-chloro-9H-purin-9-yl)dodecan-1-ol (9b) exhibited the most potent effect against the HCT-116 and SW480 cells with IC50 values of 0.89 and 1.15 μM, respectively. Furthermore, all of the (R)-configured acyclic nucleoside derivatives displayed more potent anticancer activity compared to their (S)-counterparts. Mechanistic studies revealed that compound 9b triggered apoptosis in the cancer cell lines via depolarization of the mitochondrial membrane and effectively inhibited colony formation. Importantly, compound 9b inhibited the growth of the SW480 xenograft in a mouse model with low systemic toxicity. These results indicated that acyclic nucleoside compounds are viable as potent and effective anticancer agents, and compound 9b may serve as a promising lead compound that merits further attention in future anticancer drug discovery.
- Hao, Er-Jun,Li, Gong-Xin,Liang, Yu-Ru,Xie, Ming-Sheng,Wang, Dong-Chao,Jiang, Xiao-Han,Cheng, Jia-Yi,Shi, Zhi-Xian,Wang, Yang,Guo, Hai-Ming
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supporting information
p. 2077 - 2109
(2021/02/16)
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- Divergent Total Syntheses of (?)-Huperzine Q, (+)-Lycopladine B, (+)-Lycopladine C, and (?)-4-epi-Lycopladine D
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We report herein our synthetic efforts towards the divergent syntheses of (?)-huperzine Q (1), (+)-lycopladine B (2), (+)-lycopladine C (3), and (?)-lycopladine D (4). The 10-step total synthesis of (?)-huperzine Q (1) and the first total syntheses of (+)
- Hong, Benke,Hu, Dachao,Wu, Jinbao,Zhang, Jing,Li, Houhua,Pan, Yingming,Lei, Xiaoguang
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supporting information
p. 1557 - 1567
(2017/07/11)
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- A TEMPO-free copper-catalyzed aerobic oxidation of alcohols
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The copper-catalyzed aerobic oxidation of primary and secondary alcohols without an external N-oxide co-oxidant is described. The catalyst system is composed of a Cu/diamine complex inspired by the enzyme tyrosinase, along with dimethylaminopyridine (DMAP) or N-methylimidazole (NMI). The Cu catalyst system works without 2,2,6,6-tetramethyl-l-piperidinoxyl (TEMPO) at ambient pressure and temperature, and displays activity for un-activated secondary alcohols, which remain a challenging substrate for catalytic aerobic systems. Our work underscores the importance of finding alternative mechanistic pathways for alcohol oxidation, which complement Cu/TEMPO systems, and demonstrate, in this case, a preference for the oxidation of activated secondary over primary alcohols.
- Xu, Boran,Lumb, Jean-Philip,Arndtsen, Bruce A.
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supporting information
p. 4208 - 4211
(2015/04/14)
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- Chemo-, regio-, and stereo-selective perfluoroalkylations by a Grignard complex with zirconocene
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The synthesis of highly reactive perfluoroalkyl Grignard reagents with early transition metal zirconocene complexes and their new types of highly chemo-, regio-, and stereo-selective perfluoroalkylation reactions are reported with epoxides in particular. The zirconocene complex is advantageous in activating the perfluoroalkyl Grignard species. The zirconocene·Grignard complexes were clarified by DOSY. Both 1H and 19F DOSY analyses show that the addition of MAO and dioxane to the mixture of RFMgCl and Cp2ZrCl2 connects Cp2Zr and RFMg to generate the zirconocene/perfluoroalkyl-Grignard/dioxane complex.
- Fujiu, Motohiro,Negishi, Kazuyuki,Guang, Jie,Williard, Paul G.,Kuroki, Shigeki,Mikami, Koichi
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supporting information
p. 19464 - 19468
(2015/11/27)
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- Total synthesis of isoquinocyclinone
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The total synthesis of the heptacyclic natural product isoquinocyclinone has been achieved. A Hauser annulation was used to assemble the anthraquinone core structure. The unique 2,4,5,6-tetrahydropyrrolo[2,3-b]pyrrole substructure was prepared by alkyne addition to a lactone intermediate and subsequent Ni 0-mediated cyanide addition, the conversion of an O,O- into an N,O-acetal, and final intramolecular N-alkylation. Hauser annulation: An efficient total synthesis of isoquinocyclinone was achieved using a pentacyclic lactone as the key intermediate (see scheme). The pyrrolo-pyrrole substructure was elaborated by acetylide acylation, conversion of an O,O-acetal into an N,O-acetal, and intramolecular amidine alkylation.
- Dischmann, Mike,Frassetto, Timo,Breuning, M. André,Koert, Ulrich
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supporting information
p. 11300 - 11302
(2014/10/15)
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- Oxidation of allylic and benzylic alcohols to aldehydes and carboxylic acids
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An oxidation of allylic and benzylic alcohols to the corresponding carboxylic acids is effected by merging a Cu-catalyzed oxidation using O 2 as a terminal oxidant with a subsequent chlorite oxidation (Lindgren oxidation). The protocol was optimized to obtain pure products without chromatography or crystallization. Interception at the aldehyde stage allowed for Z/E-isomerization, thus rendering the oxidation stereoconvergent with respect to the configuration of the starting material.
- K?nning, Daniel,Olbrisch, Tobias,Sypaseuth, Fanni D.,Tzschucke, C. Christoph,Christmann, Mathias
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supporting information
p. 5014 - 5016
(2014/05/06)
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- Enantioselective synthesis of 3,4-dihydro-1,2-oxazepin-5(2 H)-ones and 2,3-dihydropyridin-4(1 H)-ones from β-substituted β- hydroxyaminoaldehydes
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The synthesis of 3,4-dihydro-1,2-oxazepin-5(2H)-ones and 2,3-dihydropyridin-4(1H)-ones from β-substituted β- hydroxyaminoaldehydes is reported. The β-hydroxyaminoaldehydes were prepared by enantioselective organocatalytic 1,4-addition of N-tert-butyl (tert-butyldimethylsilyl)oxycarbamate to α,β-unsaturated aldehydes (MacMillan protocol). Alkyne addition to the aldehydes followed by alcohol oxidation furnished N-Boc O-TBS-protected β-aminoynones. Removal of the TBS protecting group initiated a 7-endo-dig cyclization to yield previously unknown 3,4-dihydro-1,2-oxazepin-5(2H)-ones. Reductive cleavage of the N-O bond of the oxazepinones and Boc-deprotection provided 2-substituted 2,3-dihydropyridin- 4(1H)-ones via 6-endo-trig cyclization. 2,3-Dihydropyridin-4(1H)-ones are versatile intermediates that have been used for the synthesis of many alkaloids. The new protocol allows the synthesis of 3-dihydropyridin-4(1H)-ones carrying an array of substituents at C2 that cannot be prepared from commercial β-amino acids or by one-carbon homologation of proteinogenic amino acids. The use of readily available β-hydroxylaminoaldehydes expands the utility of our previously reported method to prepare 2,3-dihydropyridin-4(1H)-ones from β-amino acids as the source of diversity and chirality. A broad substrate scope is possible because β-aminoaldehydes can be prepared from α,β-unsaturated aldehydes by an enantioselective organocatalytic process.
- Ranade, Adwait R.,Georg, Gunda I.
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p. 984 - 992
(2014/03/21)
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- The stereochemical course and mechanism of the IspH reaction
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On the right path: The stereochemcial course of the IspH reaction, the last reaction in the deoxyxylulose phosphate pathway to terpenes, was investigated in feeding experiments with deuterated isotopologues of 1-deoxy-D-xylulose. The results support an enzyme mechanism for IspH that involves a previously suggested metallacyclopropane intermediate. Copyright
- Citron, Christian A.,Brock, Nelson L.,Rabe, Patrick,Dickschat, Jeroen S.
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supporting information; experimental part
p. 4053 - 4057
(2012/06/01)
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- One-pot oxidation/isomerization of Z-allylic alcohols with oxygen as stoichiometric oxidant
-
A method for generating (E)-α,β-unsaturated aldehydes from Z-allylic alcohols or E/Z-mixtures is described. The one-pot procedure involves a Cu-catalyzed oxidation followed by an organocatalytic Z/E-isomerization with N,N-dimethylaminopyridine (DMAP).
- Koenning, Daniel,Hiller, Wolf,Christmann, Mathias
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supporting information
p. 5258 - 5261
(2013/01/15)
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- Dihydroxylation-based approach for the asymmetric syntheses of hydroxy-γ-butyrolactones
-
A method of preparing enantiopure hydroxy-γ-butyrolactones containing multiple contiguous stereocenters in high yield with good diastereoselectivity has been developed. Osmium tetroxide mediated dihydroxylation of a range of β-alkenyl-β-hydroxy-N-acyloxazolidin-2-ones results in formation of triols that undergo spontaneous intramolecular 5-exo-trig cyclization reactions to provide hydroxy-γ-butyrolactones. The stereochemistry of these hydroxy-γ-butyrolactones has been established using NOE spectroscopy, which revealed that 1-substituted, 1,1-disubstituted, (E)-1,2-disubstituted, (Z)-1,2-disubstituted, and 1,1,2-trisubstituted alkenes undergo dihydroxylation with anti-diastereoselectivity, while 1,2,2-trisubstituted systems afford syn-diastereoisomers. The synthetic utility of this methodology has been demonstrated for the asymmetric synthesis of the natural product 2-deoxy-d-ribonolactone. Published 2011 by the American Chemical Society.
- Peed, Jennifer,Davies, Iwan R.,Peacock, Lucy R.,Taylor, James E.,Kociok-Koehn, Gabriele,Bull, Steven D.
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p. 543 - 555
(2012/02/04)
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- Asymmetric synthesis of chiral δ-lactones containing multiple contiguous stereocenters
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A versatile methodology for the asymmetric synthesis of chiral δ-lactones containing multiple contiguous stereocenters has been developed that relies on a series of Evans' aldol, hydroxyl-directed cyclopropanation, methanolysis, and Hg(II) mediated cyclopropane ring-opening reactions for stereocontrol.
- Peed, Jennifer,Perinan Dominguez, Ignacio,Davies, Iwan R.,Cheeseman, Matt,Taylor, James E.,Kociok-Koehn, Gabriele,Bull, Steven D.
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p. 3592 - 3595
(2011/09/21)
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- Organocatalytic strategies for the construction of optically active imidazoles, oxazoles, and thiazoles
-
This study demonstrates the first enantioselective synthesis of hydroxyalkyl- and aminoalkyl-substituted imidazoles, oxazoles, and thiazoles. The approach developed utilizes a highly effective one-pot reaction cascade that consists of either an organocatalytic epoxidation or aziridination of α,β-unsaturated aldehydes coupled with a [3+2]-annulation, in which amidines, ureas, or thioureas act as effective 1,3-dinucleophilic species. The methodology described benefits from low catalyst loadings, commercially and readily available starting materials, and mild reaction conditions.
- Albrecht, ?ukasz,Ransborg, Lars Krogager,Albrecht, Anna,Lykke, Lennart,J?rgensen, Karl Anker
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supporting information; body text
p. 13240 - 13246
(2012/02/05)
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- Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis
-
The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g., Wittig and Horner-Wadsworth-Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology.
- Sirasani, Gopal,Paul, Tapas,Andrade, Rodrigo B.
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experimental part
p. 2197 - 2205
(2011/04/22)
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- An expedient asymmetric synthesis of N-protected (S, S)-2-aminomethyl-1- cyclopropanecarboxylic acid
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An enantioselective synthesis of a N-Boc-protected trans-cyclopropane γ-amino acid is reported. The key chiral aldehyde intermediate is prepared in enantiomerically pure form using a three-step aldol-cyclopropanation-retro- aldol protocol.
- Aitken, David J.,Bull, Steven D.,Davies, Iwan R.,Drouin, Ludovic,Ollivier, Jean,Peed, Jennifer
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scheme or table
p. 2729 - 2732
(2010/12/24)
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- Organocatalytic preparation of simple β-hydroxy and β-amino esters: Low catalyst loadings and gram-scale synthesis
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A combined amino- and N-heterocyclic carbene (NHC)-catalyzed one-pot reaction sequence for the synthesis of simple enantioenriched β-hydroxy and β-amino esters using commercially available catalysts at low catalyst loadings has been developed. The desired
- Jiang, Hao,Gschwend, Bjoern,Albrecht, Lukasz,Anker Jorgensen, Karl
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supporting information; experimental part
p. 5052 - 5055
(2010/12/25)
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- De novo synthesis of pentoses via cyanohydrins as key intermediates
-
A de novo synthesis of pentoses is described starting from (Z)-2-buten-1,4-diol (1). The key step is the enzyme catalysed enantioselective HCN-addition to O-protected 4-hydroxybut-2-enal using the hydroxynitrile lyase from Hevea brasiliensis, followed by an asymmetric dihydroxylation. For the cyanohydrin reaction the influence of the configuration of the double bond and of the protecting group was investigated. The dihydroxylation step was found to be influenced by the protecting group on position 4.
- Avi, Manuela,Gaisberger, Richard,Feichtenhofer, Sabine,Griengl, Herfried
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experimental part
p. 5418 - 5426
(2009/10/24)
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- Allylic fluorination via an unusual alkene Z/E isomerisation
-
The isomerisation of readily available (Z)-4-(para-methoxybenzyloxy)-1-chloro-2-butene was achieved under mild conditions to afford the much less accessible E-diastereoisomer. This was an effective substrate in Sharpless asymmetric dihydroxylation (AD) re
- Laurenson, James A.B.,Meiries, Sebastien,Percy, Jonathan M.,Roig, Ricard
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scheme or table
p. 3571 - 3573
(2009/12/01)
-
- An asymmetric total synthesis of brevisamide
-
An enantioselective synthesis of marine alkaloid brevisamide was accomplished in a convergent manner. The synthesis utilized an enantioselective hetero-Diels - Alder reaction which sets three chiral centers in compound 11. The synthesis also features a modified Wolff-Kishner reduction, Rubottom oxidation, and Suzuki - Miyaura coupling to furnish brevisamide.
- Ghosh, Arun K.,Li, Jianfeng
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supporting information; experimental part
p. 4164 - 4167
(2009/12/31)
-
- Catalytic enantioselective allylation of dienals through the intermediacy of unsaturated π-allyl complexes
-
(Chemical Equation Presented) The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester [allylB(pin)] to >,β,γ,δ-unsaturated aldehydes is described. This reaction results in a remarkable inversion of substrate olefin geometry, providing the Z,E-configured reaction product in good enantioselectivity and olefin stereoselectivity. The reaction appears to proceed by conversion of the dienal to an unsaturated B-allyl complex followed by reductive elimination via transition state II. Enantioselectivities range from 73-94% ee for a range of δ-substituted dienals when chiral ligand L3 is employed.
- Zhang, Ping,Morken, James P.
-
supporting information; scheme or table
p. 12550 - 12551
(2010/01/30)
-
- Solvent-dependent reactivity in porcine pancreatic lipase (PPL)-catalyzed hydrolysis
-
The solvent-dependent enzyme reactivity of porcine pancreatic lipase (PPL)-catalyzed hydrolysis was investigated using trans-3 and cis-(3-(benzyloxymethyl)oxiran-2-yl)methyl acetate 4 as substrates. The conversion efficiency and enantioselectivity of the
- Shen, Liu-Lan,Wang, Fang,Mun, Han-Seo,Suh, Myungkoo,Jeong, Jin-Hyun
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p. 1647 - 1653
(2008/12/21)
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- Synthesis and biological evaluation of a phosphonate analog of the natural acetyl cholinesterase inhibitor cyclophostin
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(Chemical Equation Presented) Two diastereomers of a phosphonate analog 6 of the AChE inhibitor cyclophostin were synthesized. The substitution reaction of phosphono allylic carbonate 10a with methyl acetoacetate gave the vinyl phosphonate 9a. Attempted hydrogenation/debenzylation gave an unexpected enolether lactone. Alternatively, selective hydrogenation, demethylation, cyclization and debenzylation gave the phosphonate analog of cyclophostin as a separable mixture of diastereomers 6. The trans phosphonate isomer was more active than the cis isomer against AChE from two sources.
- Bandyopadhyay, Saibal,Dutta, Supratik,Spilling, Christopher D.,Dupureur, Cynthia M.,Rath, Nigam P.
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body text
p. 8386 - 8391
(2009/04/11)
-
- An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol
-
An improved synthesis of (2E,4Z)-6-(benzyloxy)-4-bromohexa-2,4-dien-1-ol has been devised. This new route increases the throughput and yield of the diene product by circumventing a low yielding preparation of boronic acid intermediate as well as removing the need to use multi-gram quantities of highly toxic thallium salts. In the process of developing this new route, a higher yielding preparation of (E)-3-hydroxyprop-1-enylboronic acid was also achieved.
- Clarke, Paul A.,Rolla, Gabriele A.,Cridland, Andrew P.,Gill, Andrew A.
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p. 9124 - 9128
(2008/02/10)
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- Diastereoselective zinco-cyclopropanation of chiral allylic alcohols with gem-dizinc carbenoids
-
The highly diastereoselective zinco-cyclopropanation of chiral allylic alcohols using gem-dizinc carbenoids is described. The reaction produces three contiguous stereogenic centers, and the resulting chiral cyclopropylzinc derivatives can be trapped with
- Fournier, Jean-Francois,Mathieu, Simon,Charette, Andre B.
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p. 13140 - 13141
(2007/10/03)
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- Efficient and Z-selective cross-metathesis of conjugated enynes
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Equation presented. The generation of a conjugated alkynyl alkylidene has been achieved using an allyl ether moiety as an intramolecular catalyst delivery vehicle. The reaction of this intermediate with alkenes and alkynes yields conjugated enynes with Z-
- Hansen, Eric C.,Lee, Daesung
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p. 2035 - 2038
(2007/10/03)
-
- Studies on the biosynthesis of the antibiotic moenomycin A
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Feeding experiments (13C and 15N-labeled precursors) shed light on the biosynthetic origin of the chromophore (unit A of 1), the N-acetyl groups, the 4-C-methyl group of the moenuronamide unit (part F of 1), the sugar units, and the
- Schuricht, Urs,Endler, Kirsten,Hennig, Lothar,Findeisen, Matthias,Welzel, Peter
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p. 761 - 772
(2007/10/03)
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- Asymmetric epoxide cyclisation route to the F-pyran fragment of the altohyrtins and key aldol studies
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The evolution of an asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins is described, which relies on a key intramolecular cyclisation of a C43 hydroxyl group onto a C38-C39 epoxide. The C38-C39 epoxide stereochemistry was achieved through optimisation of substrate control. Key aldol studies towards coupling the F-pyran ring with an E-pyran ring precursor was investigated, but unsuccessful. (C) 2000 Elsevier Science Ltd.
- Anderson, James C.,McDermott, Benjamin P.,Griffin, Edward J.
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p. 8747 - 8767
(2007/10/03)
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- Asymmetric synthesis of the F-pyran fragment of the altohyrtins
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The asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins has been achieved through an intramolecular cyclisation of a C43 hydroxyl group onto a C38-C39 epoxide. Absolute stereochemistry was derived from an Evans boron aldol to control C40 and C41, the C42-C43 hydroxyl stereocentres from a Sharpless(-)-diethyl tartrate controlled epoxidation and the remaining stereocentres from substrate controlled diastereoselection.
- Anderson, James C.,McDermott, Benjamin P.
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p. 7135 - 7138
(2007/10/03)
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- Asymmetric synthesis of thietanose
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Syntheses of optically active thietanose, (2R,3R,4R)-4-acetoxymethyl-3-(tert-butyldimethylsilyl)oxy-2-ethoxythietane (6) and (2R,3R,4R)-3-(tertbutyldimethylsiIyl)oxy-4-[(/m-butyldimethylsilyl)oxy]methyl-2- ethoxythietane (23) are described. The key interm
- Uenishi, JuN'Ichi,Motoyama, Mitsuhiro,Kimura, Yumi,Yonemitsu, Osamu
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p. 439 - 451
(2007/10/03)
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- Synthesis of chiral 3E,5E-octadiene-1,2R-7R,8-tetraol frameworks by means of palladium(II)-promoted hetero-Claisen rearrangement: Mechanistic aspect
-
A plausible mechanism has been proposed for the exclusive formation of symmetrical dienediol such as 1,6-bis(acetoxy)-2,4-diene in palladium(II)-promoted [3,3]sigmatropic rearrangement of 3,4-bis(acetoxy)-1,5-diene system. This mechanism referred to as migration-induced intramolecular dioxanium ion switching (MIDIS) process can reasonably explain why the vicinal acetoxy groups move from 3,4-position and not to 5,6- but two directionally to 1,6-position.
- Saito, Seiki,Kuroda, Akiyoshi,Matsunaga, Hiroshi,Ikeda, Shushiro
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p. 13919 - 13932
(2007/10/03)
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- Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose
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Acetals of α,β-unsaturated aldehydes with 3-O-alkylated derivatives of 1,2-O-isopropylidene-β-D-fructopyranose and 1,2-O-isopropylidene-β-D-psicopyranose, which are readily available from D-fructose, were cyclopropanated with Et2Zn and CH2I2 with good diastereoselectivity.The effects of structure of the acetals on enantioselectivity were examined.
- Kang, Jahyo,Lim, Geun Jho,Yoon, Suk Kyoon,Kim, Moohi Yoo
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p. 564 - 577
(2007/10/02)
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- Regiochemical control of the ring opening of 1:2-epoxides by means of chelating processes. 10. Synthesis and ring opening reactions of mono- and difunctionalized cis and trans aliphatic oxirane systems
-
The regiochemical outcome of the ring opening of 1:2-epoxides through chelation processes assisted by metal ions, was verified in mono- and difunctionalized aliphatic oxirane systems bearing the heterofunctionality (OR) in an homoallylic and/or allylic relationship to the oxirane ring. The effect of the distance of the OR functionality from the oxirane ring and of the type of protective group on the regiochemical outcome of these systems is examined. In some cases, the use of LiClO4 or Mg(ClO4)2 as the promoting metal salt makes it possible the obtainment of a nice regioalternating process.
- Azzena, Francesca,Calvani, Federico,Crotti, Paolo,Gardelli, Cristina,Macchia, Franco,Pineschi, Mauro
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p. 10601 - 10626
(2007/10/02)
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- β-Phosphorylated Five-Membered Ring Nitroxides: Synthesis and ESR Study of 2-Phosphonyl-4-(hydroxymethyl)pyrrolidine Aminoxyl Radicals
-
Intramolecular aminomercuration of the alkenyl α-amino phosphonate 6 followed by sodium borohydride reduction leads to the diethyl (4-(benzyloxymethyl)-2,5,5-trimethylpyrrolidinyl)phosphonate 7.Oxidation of the phosphonates 7 and 8 with 3-chloroperbenzoic
- Stipa, Pierluigi,Finet, Jean-Pierre,Moigne, Francois Le,Tordo, Paul
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p. 4465 - 4468
(2007/10/02)
-
- Hydrolytic and Reductive Action of Fermenting Yeast on a Keto Acetate: Synthesis of (+)-endo-Brevicomin
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The keto acetate 1 in fermenting yeast gives the diol 2 with high enantiomeric excess.The product arises from hydrolysis-reduction and is transformed into (+)-endo-brevicomin.The hydroxy acetate from direct reduction of 1 is racemic.
- Petrocchi-Fantoni, Giuseppe,Servi, Stefano
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p. 1764 - 1765
(2007/10/02)
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- A mercury mediated route to the mitosenes
-
A Mitsunobu type of coupling is used to prepare a complex phenyl allyl ether which undergoes a Claisen rearrangement. A synthetic route to a mitosene is achieved.
- Danishefsky, Samuel,Regan, John
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p. 3919 - 3922
(2007/10/02)
-