Stereoselective Synthesis of the Antileukemic Sesquiterpene (+)-Caparratriene from L-menthol and Tiglic Aldehyde

被引:5
|
作者
Vydrina, V. A. [1 ]
Kravchenko, A. A. [1 ]
Yakovleva, M. P. [1 ]
Ishmuratova, N. M. [1 ]
Ishmuratov, G. Yu. [1 ]
机构
[1] Russian Acad Sci, Ufa Inst Chem, 71 Prosp Oktyabrya, Ufa 450054, Russia
关键词
(+)-caparratriene; L-menthol; tiglic aldehyde; Wittig reaction; (R)-(-)-citronellylbromide;
D O I
10.1007/s10600-018-2379-y
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A stereoselective synthesis of natural (+)-caparratriene was developed starting from commercially available L-menthol and tiglic aldehyde. The key step was a Wittig reaction of the latter with the triphenylphosphorane generated from (R)-(-)-citronellyl bromide. (+)-Caparratriene as a mixture (4:1) of 2E,4E- and 2E,4Z-stereoisomers is a known anticancer agent.
引用
收藏
页码:461 / 463
页数:3
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