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Total Synthesis of (+)-Cornexistin.

ABSTRACT: Herein, we describe the first total synthesis of (+)-cornexistin as well as its 8-epi-isomer starting from malic acid. The robust and scalable route features a Nozaki-Hiyama-Kishi reaction, an auxiliary-controlled syn-Evans-aldol reaction, and a highly efficient intramolecular alkylation to form the nine-membered carbocycle. The delicate maleic anhydride moiety of the nonadride skeleton was constructed from a ?-keto nitrile. The developed route enabled the synthesis of 165?mg (+)-cornexistin.

SUBMITTER: Steinborn C

PROVIDER: S-EPMC7540023 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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Total Synthesis of (+)-Cornexistin.

Steinborn Christian C Wildermuth Raphael E RE Barber David M DM Magauer Thomas T

Angewandte Chemie (International ed. in English) 20200818 39

Herein, we describe the first total synthesis of (+)-cornexistin as well as its 8-epi-isomer starting from malic acid. The robust and scalable route features a Nozaki-Hiyama-Kishi reaction, an auxiliary-controlled syn-Evans-aldol reaction, and a highly efficient intramolecular alkylation to form the nine-membered carbocycle. The delicate maleic anhydride moiety of the nonadride skeleton was constructed from a β-keto nitrile. The developed route enabled the synthesis of 165 mg (+)-cornexistin. ...[more]

PMID: 32558114

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