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

Author:
Chen, Renzhi, Li, Linbin, Lin, Na, Zhou, Rong, Hua, Yuhui, Deng, Hejun, Zhang, Yandong
Source:
Organic letters 2018 v.20 no.5 pp. 1477-1480
ISSN:
1523-7052
Subject:
dimerization, enantiomers, fatty acids
Abstract:
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.
Agid:
6083669