An enantioselective total synthesis of pinnaic acid

被引：52

作者：

Hao Wu ^{[1
]}

Honglu Zhang ^{[1
]}

Gang Zhao ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Modern Synthet Organ Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2007年 / 63卷 / 28期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tet.2007.03.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective and convergent total synthesis of marine natural product pinnaic acid has been achieved. Our general synthetic approach is featured with an asymmetric hydrogenation of racemic gamma-keto ester 3, a diastereoselective methylation on the alpha-methylene of the (1R,5R)-lactone 4, and a diastereoselective Michael addition of the tertiary nitro cyclopentane. The central azaspiro[4.5] decane was constructed utilizing reductive cyclization of the delta-nitroketone followed by highly stereoselective reduction of the cyclic imine with NaBH4. Ultimately, successive use of triethyl-2-phosphonopropionate and Heathcock's phosphorane 18 to elaborate C5 and C13 side chains completed the total synthesis of pinnaic acid. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：6454 / 6461

页数：8

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