Structural Revision of (+)-Uprolide F Diacetate Confirmed by Asymmetric Total Synthesis

被引：24

作者：

Zhu, Liangyu ^{[1
]}

Tong, Rongbiao ^{[1
]}

机构：

[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 08期

基金：

中国国家自然科学基金;

关键词：

MARINE NATURAL-PRODUCTS; CORAL SARCOPHYTON-CRASSOCAULE; BAYLIS-HILLMAN REACTION; METHYLENE-GAMMA-BUTYROLACTONES; GORGONIAN EUNICEA-MAMMOSA; SOFT CORAL; STEREOSELECTIVE-SYNTHESIS; SINULARIA-FLEXIBILIS; EUPALMERIN ACETATE; UPROLIDE-D;

D O I：

10.1021/acs.orglett.5b00700

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new structure for the cytotoxic cembranolide uprolide F diacetate (UFD) was proposed, and an enantioselective total synthesis was accomplished to confirm that our revised structure correctly represented the natural UFD and its absolute configuration. Our synthesis features a late-stage, highly efficient, and diastereoselective NozakiHiyamaKishi macrocyclization (95% yield) and an unexpected reagent-controlled reversible translactonization, which, being the first example within the cembranolide family, might have biogenetic implications and be of great importance to synthetic studies of the a-methylene-?-lactone-bearing cembranolides.

引用

页码：1966 / 1969

页数：4

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