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Total Synthesis of the Reported Structure of Neaumycin B.

ABSTRACT: The stereoselective total synthesis of structure 1 assigned to the macrolide natural product neaumycin B is reported in a 2.3% overall yield on 90 mg scale. The synthesis features a gram-scale nickel-catalyzed reductive cross-coupling/spiroketalization tactic to construct the spiroketal core of neaumycin B. The stereostructures of the C3-C6, C8-C14, and C20-C41 segments of synthetic neaumycin B were unambiguously verified by X-ray crystallography.

SUBMITTER: Ding J

PROVIDER: S-EPMC10848393 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature

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Total Synthesis of the Reported Structure of Neaumycin B.

Ding Jiaming J Smith Amos B AB

Journal of the American Chemical Society 20230810 33

The stereoselective total synthesis of structure <b>1</b> assigned to the macrolide natural product neaumycin B is reported in a 2.3% overall yield on 90 mg scale. The synthesis features a gram-scale nickel-catalyzed reductive cross-coupling/spiroketalization tactic to construct the spiroketal core of neaumycin B. The stereostructures of the C3-C6, C8-C14, and C20-C41 segments of synthetic neaumycin B were unambiguously verified by X-ray crystallography. ...[more]

PMID: 37561549

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