Catalytic Enantioselective Total Syntheses of Bakkenolides I, J, and S: Application of a Carbene-Catalyzed Desymmetrization

被引：70

作者：

Phillips, Eric M. ^{[1
]}

Roberts, John M. ^{[1
]}

Scheidt, Karl A. ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Ctr Mol Innovat & Drug Discovery, Chem Life Proc Inst, Evanston, IL 60208 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 12期

关键词：

STEREOCONTROLLED TOTAL-SYNTHESIS; CARBONYL RADICAL CYCLIZATION; N-HETEROCYCLIC CARBENES; BETA-KETOESTERS; EFFICIENT; (+/-)-BAKKENOLIDE-A; BAKKANES; RING; (-)-9-ACETOXYFUKINANOLIDE; (-)-HOMOGYNOLIDE-A;

D O I：

10.1021/ol100938j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general strategy for the catalytic asymmetric syntheses of the bakkenolides is reported. The key bond-forming step Involves an N-heterocyclic carbene catalyzed desymmetrization of a 1,3-diketone to form three new bonds in one step with excellent enantio- and diastereoselectivity. This intramolecular reaction allows direct access to the hydrindane core of the bakkenolide family and enables a facile synthesis of these natural products.

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页码：2830 / 2833

页数：4

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