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 β-keto nitrile. The developed route enabled the synthesis of 165 mg (+)-cornexistin.

SUBMITTER: Steinborn C 

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

REPOSITORIES: biostudies-literature