Asymmetric Total Synthesis of (+)-Majusculoic Acid via a Dimerization-Dedimerization Strategy and Absolute Configuration Assignment

被引:18
|
作者
Chen, Renzhi
Li, Linbin
Lin, Na
Zhou, Rong
Hua, Yuhui
Deng, Hejun
Zhang, Yandong [1 ]
机构
[1] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China
关键词
CONTAINING NATURAL-PRODUCTS; FATTY-ACIDS; MARINE CYANOBACTERIUM; CONFORMATION DESIGN; METATHESIS REACTION; OLEFIN METATHESIS; SPONGE; RINGS;
D O I
10.1021/acs.orglett.8b00349
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of (+)-majusculoic acid, the enantiomer of naturally occurring antifungal cyclopropane fatty acid (-)-majusculoic acid, was accomplished in 13 steps, leading to the assignment of the absolute configuration of the natural product. The synthesis featured a ring closing metathesis dimerization, a conformationally controlled cyclopropanation, a dedimerization, and a bromoolefination.
引用
收藏
页码:1477 / 1480
页数:4
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