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Asymmetric Total Synthesis of the Naturally Occurring Antibiotic Anthracimycin.

ABSTRACT: The first total synthesis of the potent antibiotic anthracimycin was achieved in 20 steps. The synthesis features an intramolecular Diels-Alder reaction to forge the trans-decalin moiety, and an unprecedented aldol reaction using a complex β-ketoester to provide the tricarbonyl motif. A Stork-Zhao olefination and Grubbs ring closing metathesis delivered the E/Z-diene and forged the macrocycle. The C2 configuration was set with a base-mediated epimerization, providing access to (-)-anthracimycin.

SUBMITTER: Davison EK

PROVIDER: S-EPMC8283552 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Asymmetric Total Synthesis of the Naturally Occurring Antibiotic Anthracimycin.

Davison Emma K EK Freeman Jared L JL Zhang Wanli W Wuest William M WM Furkert Daniel P DP Brimble Margaret A MA

Organic letters 20200629 14

The first total synthesis of the potent antibiotic anthracimycin was achieved in 20 steps. The synthesis features an intramolecular Diels-Alder reaction to forge the trans-decalin moiety, and an unprecedented aldol reaction using a complex β-ketoester to provide the tricarbonyl motif. A Stork-Zhao olefination and Grubbs ring closing metathesis delivered the E/Z-diene and forged the macrocycle. The C2 configuration was set with a base-mediated epimerization, providing access ...[more]

PMID: 32598151

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