A Concise Enantioselective Synthesis of the Chlorosulfolipid Malhamensilipin A

被引：55

作者：

Bedke, D. Karl ^{[1
]}

Shibuya, Grant M. ^{[1
]}

Pereira, Alban R. ^{[2
]}

Gerwick, William H. ^{[2
]}

Vanderwal, Christopher D. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

[2] Univ Calif San Diego, Scripps Inst Oceanog, Ctr Marine Biotechnol & Biomed, La Jolla, CA 92093 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 08期

关键词：

CATALYTIC ASYMMETRIC DIHYDROXYLATION; OCHROMONAS-DANICA; ADRIATIC MUSSELS; STEREOCHEMISTRY; SHELLFISH; MOTIFS; LIPIDS; TOXINS;

D O I：

10.1021/ja910809c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective synthesis of a member of the chlorosulfolipid family of natural products is reported. All of the polar substituents of malhamensilipin A are introduced with high stereoselectivity, and the unique (E)-chlorovinyl sulfate is created by a chemo-, regio-, and stereoselective E2 elimination of HCl in a reaction that likely has a counterpart in the biosynthesis of this fascinating natural product.

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收藏

页码：2542 / +

页数：3

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