Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine [Jaspine B]

被引：59
|
作者：
Prasad, Kavirayani R. [1 ]
Chandrakumar, Appayee [1 ]
机构：
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 16期
关键词：
D O I：
10.1021/jo0707838
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine.
引用
收藏
页码：6312 / 6315
页数：4
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