Asymmetric Total Synthesis of (+)-Majusculoic Acid via a Dimerization–Dedimerization Strategy and Absolute Configuration Assignment
Renzhi Chen, Linbin Li, Na Lin, Rong Zhou, Yuhui Hua, Hejun Deng, Yandong Zhang
Abstract
Renzhi Chen, Linbin Li, Na Lin, Rong Zhou, Yuhui Hua, Hejun Deng, Yandong Zhang
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.
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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.
Key concepts: Absolute configuration, Chemistry, Total synthesis, Cyclopropanation, Cyclopropane, Metathesis, Enantiomer, Stereochemistry