2018Organic LettersRequires access

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

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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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What this paper is about

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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Available 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.

Key concepts: Absolute configuration, Chemistry, Total synthesis, Cyclopropanation, Cyclopropane, Metathesis, Enantiomer, Stereochemistry

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