A short enantioselective synthesis of 3-epi-jaspine B and (+)-oxybiotin via an intramolecular tandem desilylation oxa-Michael addition strategy

被引：15

作者：

Shelke, Anil M. ^{[1
]}

Rawat, Varun ^{[1
]}

Sudalai, Arumugam ^{[1
]}

Suryavanshi, Gurunath ^{[1
]}

机构：

[1] Natl Chem Laboratoty, Chem Engn & Proc Dev Div, Pune 411008, Maharashtra, India

来源：

RSC ADVANCES | 2014年 / 4卷 / 91期

关键词：

PACHASTRISSAMINE JASPINE B; STEREOSELECTIVE-SYNTHESIS; STEREOSPECIFIC SYNTHESIS;

D O I：

10.1039/c4ra08698h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new synthesis of cytotoxic anhydrophytosphingosine 3-epi-jaspine B (34.7% overall yield; 97% ee) and (+)-oxybiotin (21.2% overall yield; 97% ee), bioactive oxygen analogue of biotin, is described starting from commercially available cis-2-butene-1,4-diol. The key reactions employed in the synthesis include Sharpless asymmetric epoxidation and a novel tandem desilylation oxa-Michael addition reaction strategy to construct a tetrahydrofuran core (dr > 99%).

引用

页码：49770 / 49774

页数：5

共 20 条

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