Total synthesis of (+)-13-deoxytedanolide

被引：48

作者：

Julian, LD ^{[1
]}

Newcom, JS ^{[1
]}

Roush, WR ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 17期

关键词：

D O I：

10.1021/ja050729d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A total synthesis of 13-deoxytedanolide is described. The synthesis features a highly stereoselective fragment assembly aldol reaction of methyl ketone 4 and aldehyde 5 to establish the complete carbon skeleton of the natural product in the form of aldol 15. The facile formation of the remarkably unreactive hemiketal 16 thwarted attempts to elaborate 15 to tedanolide. However, deoxygenation of the C(13)-hydroxyl of 16 provided the 13-deoxy hemiketal 17 that was smoothly elaborated to 13-deoxytedanolide. Copyright © 2005 American Chemical Society.

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页码：6186 / 6187

页数：2

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