91376-49-7Relevant academic research and scientific papers
A convergent approach for the total synthesis of the α-glucosidase inhibitor (-)-panaxjapyne-C
Sathish Reddy,Gangadhar,Srihari
, p. 1524 - 1530 (2013/12/04)
The stereoselective total synthesis of (-)-panaxjapyne-C was accomplished in a convergent fashion. The synthesis utilizes the readily available enantiomers l-(+)-diethyltartrate and d-(-)-diethyltartrate and involves a Cadiot-Chodkiewicz coupling reaction, and an Ohira-Bestmann reaction as the key steps.
Natural feedstocks for diversity-oriented synthesis: Macrolide-like scaffolds from nonactate
Sumskaya, Yuliya G.,Swain, P. Whitney,Bergmeier, Stepehen C.,McMills, Mark C.,Priestley, Nigel D.,Wrighta, Dennis L.
experimental part, p. 144 - 166 (2011/07/07)
We have been interested in the application of readily available, fermentation-derived natural products as key building blocks for the preparation of natural product-like libraries rich in structural and stereochemical diversity. In this manuscript we describe the conversion of methyl nonactate, derived from nonactin, to a diversable scaffold characteristic of macrolide natural products. The synthesis features a key ring-closing metathesis reaction to form the macrocycle. ARKAT-USA, Inc.
A modular approach to aryl-C-ribonucleosides via the allylic substitution and ring-closing metathesis sequence. A stereocontrolled synthesis of all four α-/β- and D-/L-C-nucleoside stereoisomers
Stambasky, Jan,Kapras, Votech,Stefko, Martin,Kysilka, Ondrej,Hocek, Michal,Malkov, Andrei V.,Kocovsky, Pavel
experimental part, p. 7781 - 7803 (2011/12/14)
Iridium(I)-catalyzed allylation of the enantiopure monoprotected copper(I) alkoxide, generated from (S)-5a, with the enantiopure allylic carbonates (R)-9a,b has been developed as the key step in a new approach to C-nucleoside analogues. The anomeric cente
Enantioselective synthesis of cyclic, quaternary oxonitriles
Guenes, Yakup,Polat, M. Fatih,Sahin, Ertan,Fleming, Fraser F.,Altundas, Ramazan
supporting information; experimental part, p. 7092 - 7098 (2010/12/24)
Quaternary oxonitriles are stereoselectively generated from the union of five-, six-, and seven-membered 2-chloroalkenecarbonitriles with chiral alcohols via a Claisen rearrangement. The strategy rests on a new conjugate addition-elimination of allylic alkoxides to 2-chlorocycloalkenecarbonitriles to afford substituted 2-alkoxyalkenenitriles. Subsequent thermolysis unmasks a cyclic oxonitrile while selectively forming a new quaternary center with enantiomeric ratios typically greater than 9:1. The overall alkylation strategy addresses the challenge of enantioselectively generating hindered, quaternary centers while simultaneously installing ketone, nitrile, and olefin functionalities.
Synthesis of 3-vinyl-2,5-dihydrofuran ring system via enyne metathesis
Vuong, Sophie,Mercedes Rodriguez-Fernandez,Renoux, Brigitte,Len, Christophe
experimental part, p. 324 - 329 (2010/03/26)
An efficient route, starting from but-3-en-1,2-diol, is described to synthesize racemic diastereoisomeric (5-ethoxy-4-vinyl-2,5-dihydrofuran-2-yl) methanol derivatives. Acyclic enyne intermediates having the alkyne moiety directly connected to the asymmet
Enantioselective total synthesis of brevetoxin A: Unified strategy for the B, E, G, and J subunits
Crimmins, Michael T.,Ellis, J. Michael,Emmitte, Kyle A.,Haile, Pamela A.,McDougall, Patrick J.,Parrish, Jonathan D.,Zuccarello, J. Lucas
supporting information; experimental part, p. 9223 - 9234 (2010/04/25)
Brevetoxin A is a decacyclic ladder toxin that possesses 5-, 6-, 7-, 8-, and 9-membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring-closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium-ring ethers. The strategies developed for the syntheses of these four monocycles ultimately provided multigram quantities of each of the rings, supporting our efforts toward the completion of a convergent synthesis of brevetoxin A.
A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin
Kadota, Isao,Abe, Takashi,Uni, Miyuki,Takamura, Hiroyoshi,Yamamoto, Yoshinori
, p. 3643 - 3647 (2008/09/20)
Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring.
3-vinyl-2,5-dihydrofuran derivatives via enyne metathesis
Rodriguez-Fernandez, M. Mercedes,Vuong, Sophie,Renoux, Brigitte,Len, Christophe
, p. 1703 - 1706 (2007/12/28)
Acyclic enynes having the alkyne moiety directly connected to the asymmetric carbon atom of an acetal were obtained in two steps. These reactive substrates were then subjected to ruthenium-catalyzed enyne metathesis to produce (5-ethoxy-4-vinyl-2,5-dihydr
Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A
Crimmins, Michael T.,Zuccarello, J. Lucas,Cleary, Pamela A.,Parrish, Jonathan D.
, p. 159 - 162 (2007/10/03)
(Chemical Equation Presented) A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi-Sakurai reactions were central operations in the construction of the G ring and J ring subunits, which were united through a Horner-Wadsworth-Emmons coupling. Subsequent dehydrative cyclization produced an endocyclic enol ether that was further elaborated to the tetracyclic GHIJ fragment of brevetoxin A.
Zinc(II) triflate-controlled 1,3-dipolar cycloadditions of C-(2-thiazolyl)nitrones: Application to the synthesis of a novel isoxazolidinyl analogue of tiazofurin
Chiacchio, Ugo,Rescifina, Antonio,Saita, Maria G.,Iannazzo, Daniela,Romeo, Giovanni,Mates, Juan A.,Tejero, Tomas,Merino, Pedro
, p. 8991 - 9001 (2007/10/03)
The cycloaddition reaction between C-(2-thiazolyl) nitrones and allylic alcohol takes place with complete exo selectivity when the reactions are carried out in the presence of 1 equiv of zinc triflate. The rate of the reaction is increased enormously unde
