Total Synthesis of (-)-Lepadiformine A via Radical Translocation-Cyclization Reaction

Masashi Shimomura, Manabu Sato, Hiroki Azuma, Juri Sakata, Hidetoshi Tokuyama

Research output: Contribution to journalArticle

Abstract

Total synthesis of (-)-lepadiformine A featuring construction of the 1-azaspiro[4.5]decane skeleton by a highly diastereoselective radical translocation-cyclization reaction of a γ-lactam derivative bearing a chiral butenolide moiety is described. The enantioselective construction of butenolide is conducted via Krische's catalytic asymmetric allylation protocol. After the radical translocation-cyclization reaction, a hydroxymethyl group at the C-13 position was stereoselectively introduced by a one-pot partial reduction-allylation protocol of the unprotected lactam derivative. Finally, the total synthesis is completed by formation of a C ring.

Original languageEnglish
Pages (from-to)3313-3317
Number of pages5
JournalOrganic letters
Volume22
Issue number9
DOIs
Publication statusPublished - 2020 May 1

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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