Topic
Total synthesis
About: Total synthesis is a research topic. Over the lifetime, 25578 publications have been published within this topic receiving 489319 citations.
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TL;DR: In this paper, the chiral Rh2(MPPIM)4 catalysts were applied to fully aliphatic systems resulting in the formation of β-substituted-γ-butyrolactones with high regiocontrol and with 93−96% ee.
Abstract: Intramolecular insertion into unactivated prochiral C−H bonds of 3-aryl-1-propyl diazoacetates catalyzed by dirhodium(II) tetrakis[methyl 1-(3-phenyl propanoyl)imidazolidin-2-one-4(R or S)-carboxylate], Rh2(4R-MPPIM)4 or Rh2(4S-MPPIM)4, occurs in 91−96% ee and with virtually complete regiocontrol for the formation of β-benzyl-γ-butyrolactones. This methodology has been applied to the total synthesis of dibenzylbutyrolactone lignans (−)- and (+)-enterolactone, (−)- and (+)-hinokinin, and (+)-arctigenin from substituted cinnamic acids in 19−27% overall yields. Aryltetralin lignan (+)-isodeoxypodophyllotoxin was prepared from the reactant 3,4-(methylenedioxy)cinnamic acid in 36% yield overall, and the lactone precursor to (+)-isolauricerisinol was formed in 96.5% ee and 23% yield overall. Applications of the chiral Rh2(MPPIM)4 catalysts to fully aliphatic systems resulting in the formation of β-substituted-γ-butyrolactones with high regiocontrol and with 93−96% ee have demonstrated the generality of this met...
127 citations
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TL;DR: A concise total synthesis of the tricyclic terpene cyanthiwigin U has been accomplished in 12 steps and 17% overall yield.
Abstract: A concise total synthesis of the tricyclic terpene cyanthiwigin U has been accomplished in 12 steps and 17% overall yield. The key step of the synthesis is a two-directional tandem metathesis reaction that forms the cyclohepta[e]indene core from a readily available bicyclo[2.2.2]octene.
127 citations
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TL;DR: This review provides a comprehensive survey of methods used for stereoselective construction of carbon-nitrogen bonds during the total synthesis of nitrogen-containing natural products that have appeared in the literature since 2000.
Abstract: The main objective of this review is to provide a comprehensive survey of methods used for stereoselective construction of carbon–nitrogen bonds during the total synthesis of nitrogen-containing natural products that have appeared in the literature since 2000. The material is organized by specific reaction in order of decreasing number of applications in natural product synthesis. About 800 total syntheses of natural products with stereogenic carbon–nitrogen bonds described since 2000 have been reviewed.
127 citations
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127 citations
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TL;DR: This total synthesis of fungal metabolites has taken advantage of microwave heating to shorten reaction times as well as increase yields for the preparation of vital intermediates.
Abstract: Concise asymmetric total syntheses of the fungal metabolites (-)-stephacidin A, (+)-stephacidin B, and (+)-notoamide B are described. Key features of these total syntheses include (1) a facile synthesis of (R)-allyl proline methyl ester, (2) a revised route toward the pyranoindole ring system, (3) a novel cross-metathesis strategy for the introduction of important functional groups, and (4) an SN2' cyclization to form the [2.2.2] bridged bicyclic ring system. Furthermore, our synthesis has taken advantage of microwave heating to shorten reaction times as well as increase yields for the preparation of vital intermediates.
126 citations