Enzymatic lactonization stategy for enantioselective synthesis of a tetrahydrolipstatin synthon

被引：18

作者：

Sharma, A ^{[1
]}

Chattopadhyay, S ^{[1
]}

机构：

[1] Bhabha Atom Res Ctr, Div Bioorgan, Bombay 400085, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 22期

关键词：

D O I：

10.1021/jo990370+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel lipase-catalyzed protocol has been formulated for the simultaneous enantiocontrol of three stereogenic centers in a flexible acyclic system. This involved a porcine pancreatic lipase (PPL)-catalyzed delta-lactonization of a racemic 3,5-dihydroxy-2-alkyl ester to produce the lactone with high enantioselectivity (92.8%). The product lactone and its analogues are useful synthons for the asymmetric synthesis of various bioactive compounds, which include the potential anti-obesity compound, tetrahydrolipstatin.

引用

页码：8059 / 8062

页数：4

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