Total synthesis of the natural product EBC-329

被引:9
作者
Thombal, Raju S. [1 ]
Jadhav, Vrushali H. [1 ]
机构
[1] CSIR, Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India
关键词
TERRESTRIAL ORIGIN; CASBANE DITERPENOIDS; BIOLOGICAL-ACTIVITY; CROTON-INSULARIS; PHORBOL ESTERS; SOFT CORAL;
D O I
10.1039/c5ob01276g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of an anti-leukemic diterpene natural product EBC-329 (1) has been accomplished starting from readily available 6,6-dimethyl-3-oxabicyclo[3.1.0] hexane-2,4-dione (7). An efficient and general approach has been reported for the synthesis of EBC-329 in 13 steps with an overall yield of 10%.
引用
收藏
页码:9485 / 9491
页数:7
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