SYNTHESIS OF A CYANOBACTERIAL SULFOLIPID - CONFIRMATION OF ITS STRUCTURE, STEREOCHEMISTRY, AND ANTI-HIV-1 ACTIVITY

被引：68

作者：

GORDON, DM ^{[1
]}

DANISHEFSKY, SJ ^{[1
]}

机构：

[1] YALE UNIV,DEPT CHEM,NEW HAVEN,CT 06511

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1992年 / 114卷 / 02期

关键词：

D O I：

10.1021/ja00028a036

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of a cyanobacterial sulfolipid is described. The key steps involve the epoxidation of a glycal followed by conversion to a 1-beta-fluoro-2-alpha-hydroxy moiety. After protection of the alcohol, the anomeric beta-fluoro substituent is used to fashion an alpha-glycoside of a glycerol. A sulfonic acid is introduced at the 6-position by oxidation of a thioacetate with Oxone in the presence of a triene subunit.

引用

页码：659 / 663

页数：5

共 25 条

[1]

ACTON E, 1991, COMMUNICATION

[2]

BERKOWITZ DD, 1991, COMMUNICATION

[3]

CARDELLINA JH, 1991, COMMUNICATION

[4]

Danishefsky S. J., 1986, ALDRICHIM ACTA, V19, P59