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Enantioselective Synthesis of Sealutomicin C.

ABSTRACT: The sealutomicins are a family of anthraquinone antibiotics featuring an enediyne (sealutomicin A) or Bergman-cyclized aromatic ring (sealutomicins B-D). Herein we report the development of an enantioselective organocatalytic method for the synthesis of dihydroquinolines and the use of the developed method in the total synthesis of sealutomicin C which features a transannular cyclization of an aryllithium onto a γ-lactone as a second key step.

SUBMITTER: Astle SM

PROVIDER: S-EPMC11228992 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature

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Enantioselective Synthesis of Sealutomicin C.

Astle Stuart M SM Guggiari Sean S Frost James R JR Hepburn Hamish B HB Klauber David J DJ Christensen Kirsten E KE Burton Jonathan W JW

Journal of the American Chemical Society 20240617 26

The sealutomicins are a family of anthraquinone antibiotics featuring an enediyne (sealutomicin A) or Bergman-cyclized aromatic ring (sealutomicins B-D). Herein we report the development of an enantioselective organocatalytic method for the synthesis of dihydroquinolines and the use of the developed method in the total synthesis of sealutomicin C which features a transannular cyclization of an aryllithium onto a γ-lactone as a second key step. ...[more]

PMID: 38885121

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