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
收藏
页码：49770 / 49774
页数：5
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