American Chemical Society
ol8b00349_si_001.pdf (2.46 MB)

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

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journal contribution
posted on 2018-02-15, 13:20 authored by Renzhi Chen, Linbin Li, Na Lin, Rong Zhou, Yuhui Hua, Hejun Deng, Yandong Zhang
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.