Stereocontrolled Preparation of Fully Substituted Cyclopentanes: Relevance to Total Synthesis

被引：96

作者：

Heasley, Brian ^{[1
]}

机构：

[1] Scynexis Inc, Res Triangle Pk, NC 27709 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 10期

关键词：

Natural products; Carbocycles; Cyclopentane; Total synthesis; Asymmetric synthesis; Diels-Alder reaction; Palau'amine; FORMAL TOTAL-SYNTHESIS; DIELS-ALDER REACTIONS; ENANTIOSELECTIVE SYNTHESIS; RELATIVE CONFIGURATION; CORE; PALAUAMINE; TREHAZOLIN; (+)-TREHAZOLIN; MASSADINE; ALKALOIDS;

D O I：

10.1002/ejoc.200801229

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This Microreview aims to identify important advances in the asymmetric synthesis of fully substituted five-membered carbocyclic ring systems. Recent efforts directed towards the intricate and densely functionalized core substructures of three distinct classes of cyclopentane-based natural products will be examined. Strategies featuring high levels of stereocontrol and/or conciseness in the total number of synthetic steps required to access complex natural product ring fragments are highlighted. Stereoselective Diels-Alder cycloaddition approaches to access functionalized norbornene intermediates as latent chiral cyclopentanes in the tradition of Corey's elegant prostaglandin studies are a recurring theme. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：1477 / 1489

页数：13

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