A two-directional approach to a (-)-dictyostatin C11-C23 segment: Development of a highly diastereoselective, kinetically-controlled Meerwein-Ponndorf-Verley reduction

被引：27

作者：

Dilger, Andrew K. ^{[1
]}

Gopalsamuthiram, Vijay ^{[1
]}

Burke, Steven D. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 51期

关键词：

D O I：

10.1021/ja077336u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A three-step synthesis of a precursor to the C11-C23 segment of (-)-dictyostatin is described. The sequence features a sonication-assisted, enantioselective double hetero Diels-Alder (HDA) reaction catalyzed by Jacobsen's Cr(III) Schiff base catalyst, followed by a novel, highly diastereoselective Meerwein-Ponndorf-Verley (MPV) reduction of the hydropyranone subunits under kinetic control to yield the bis(axial alcohol) 4. Generalized studies of both the HDA and MPV methodologies are also described.

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页码：16273 / 16277

页数：5

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