SYNTHESIS OF A CYANOBACTERIAL SULFOLIPID - CONFIRMATION OF ITS STRUCTURE, STEREOCHEMISTRY, AND ANTI-HIV-1 ACTIVITY
SYNTHESIS OF A CYANOBACTERIAL SULFOLIPID - CONFIRMATION OF ITS STRUCTURE, STEREOCHEMISTRY, AND ANTI-HIV-1 ACTIVITY
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DOI：
10.1021/ja00028a036
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发表时间：
1992-01-15
影响因子：
15
通讯作者：
DANISHEFSKY, SJ
中科院分区：
文献类型：
--
作者：
GORDON, DM;DANISHEFSKY, SJ
介绍了一种蓝藻硫脂的全合成。关键步骤包括糖的环氧化，然后转化为1-β-氟-2-α-羟基部分。在保护醇之后，异头β-氟取代基用于形成甘油的α-糖苷。通过在三烯亚基存在下用过硫酸氢钾氧化硫代乙酸酯在6位引入磺酸。
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.