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Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J.

ABSTRACT: The family of anti-fungal natural products known as the ambruticins are structurally distinguished by a pair of pyran rings adorning a divinylcyclopropane core. Previous characterization of their biosynthesis, including the expression of a genetically modified producing organism, revealed that the polyketide synthase pathway proceeds via a diol intermediate, known as ambruticin J. Herein, we report the first enantioselective total synthesis of the putative PKS product, ambruticin J, according to a triply convergent synthetic route featuring a Suzuki-Miyaura cross-coupling and a Julia-Kocienski olefination for fragment assembly. This synthesis takes advantage of synthetic methodology previously developed by our laboratory for the stereoselective generation of the trisubstituted cyclopropyl linchpin.

SUBMITTER: Trentadue K

PROVIDER: S-EPMC8328920 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J.

Trentadue Kathryn K Chang Chia-Fu CF Nalin Ansel A Taylor Richard E RE

Chemistry (Weinheim an der Bergstrasse, Germany) 20210527 43

The family of anti-fungal natural products known as the ambruticins are structurally distinguished by a pair of pyran rings adorning a divinylcyclopropane core. Previous characterization of their biosynthesis, including the expression of a genetically modified producing organism, revealed that the polyketide synthase pathway proceeds via a diol intermediate, known as ambruticin J. Herein, we report the first enantioselective total synthesis of the putative PKS product, ambruticin J, according to ...[more]

PMID: 33887073

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