4.6 Article

Total Synthesis of (+)-(2′S,3′R)-Zoapatanol Exploiting the B-Alkyl Suzuki Reaction and the Nucleophilic Potential of the Sulfinyl Group

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 17, 期 30, 页码 8487-8494

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WILEY-BLACKWELL
DOI: 10.1002/chem.201003666

关键词

asymmetric synthesis; cross-coupling; natural products; oxepanes; total synthesis

资金

  1. CSIR, New Delhi
  2. DST, New Delhi

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A stereoselective synthesis of the diterpenoid oxepane (+)-zoapatanol is described. The key steps include a B-alkyl Suzuki cross-coupling reaction for the stereoselective synthesis of trisubstituted alkenes, creation of the two stereogenic centers on the oxepane ring by heterofunctionalization of an alkene through substrate control exploiting the nucleophilic potential of an intramolecular sulfinyl group, and transformation of a beta-hydroxy sulfoxide into a terminal alkene.

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