First comprehensive bakkane approach:: Stereoselective and efficient dichloroketene-based total syntheses of (±)- and (-)-9-acetoxyfukinanolide, (±)- and (+)-bakkenolide A, (-)-bakkenolides III, B, C, H, L, V, and X, (±)- and (-)-homogynolide A, (±)-homogynolide B, and (±)-palmosalide C

被引：72

作者：

Brocksom, TJ ^{[1
]}

Coelho, F ^{[1
]}

Deprés, JP ^{[1
]}

Greene, AE ^{[1
]}

de Lima, MEF ^{[1
]}

Hamelin, O ^{[1
]}

Hartmann, B ^{[1
]}

Kanazawa, AM ^{[1
]}

Wang, YY ^{[1
]}

机构：

[1] Univ Grenoble 1, LEDSS, F-38041 Grenoble, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 51期

关键词：

D O I：

10.1021/ja0208456

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cycloaddition of dichloroketene with dimethylcyclohexenes has been used as the key reaction in an efficient, general approach to the bakkanes. New methods and methodologies that have been developed in this work include spiro beta-methylene-gamma-butyrolactonizations, a vicinal dicarboxylation, an angelic ester preparation, a transesterification, an epoxy ketone double reduction, and a retro aldol-aldol approach to low-energy aldol isomers.

引用

页码：15313 / 15325

页数：13

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[2]

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