4.8 Article

Total Synthesis of (-)-Batrachotoxinin A: A Local-Desymmetrization Approach

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 8, Pages 3675-3679

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b12882

Keywords

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Funding

  1. Peking-Tsinghua Center for Life Sciences, Beijing National Laboratory for Molecular Sciences
  2. National Science Foundation of China [31521004, 21672011, 21822101]
  3. National Key Research and Development Program of China [2017YFA0104003]
  4. High-Performance Computing Platform of Peking University
  5. PKUAIC
  6. College of Chemistry and Molecular Engineering, Peking University

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An enantioselective total synthesis of (-)-batrachotoxinin A is accomplished based on a key photoredox coupling reaction and the subsequent local-desymmetrization operation. After the expedient assembly of the highly oxidized steroid skeleton, a delicate sequence of redox manipulations was carried out to deliver a late-stage intermediate on gram scale-and ultimately (-)-batrachotoxinin A in an efficient manner.

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