Synthetic studies on daphnicyclidin A: enantiocontrolled construction of the BCD ring system

Shuhei Ikeda, Masatoshi Shibuya, Naoki Kanoh, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

54 Citations (Scopus)

Abstract

An enantiocontrolled entry to the tricyclic core of daphnicyclidin A with five chlral centers Including an all-carbon quaternary center Is reported. The synthesis features a highly dlastereoselectlve conjugate addition of nltromethane, an Ireland- Clalsen rearrangement, and a tandem acyliminium/ Mannich- type reaction.

Original languageEnglish
Pages (from-to)1833-1836
Number of pages4
JournalOrganic letters
Volume11
Issue number8
DOIs
Publication statusPublished - 2009 Apr 16

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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