Alternative synthetic approach for (+)-phomopsidin via the highly stereoselective TADA reaction

Nobuyuki Hayashi, Takahiro Suzuki, Kenji Usui, Masahisa Nakada

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

This manuscript describes an alternative synthetic approach for (+)-phomopsidin, which shows strong inhibitory activity against the assembly of microtubule proteins. We observed that the TADA reaction of the macrolactone 5 with the reversed C11 configuration provided the desired cycloadduct 6 in 86% yield with excellent stereoselectivity (dr=16:1). Luche reduction of the ketone derived from the major product of the TADA reaction resulted in a 91% yield with excellent stereoselectivity (dr=21:1), and the major product was successfully converted to the known compound in the previously reported total synthesis of (+)-phomopsidin, thereby accomplishing the formal total synthesis of (+)-phomopsidin.

Original languageEnglish
Pages (from-to)888-895
Number of pages8
JournalTetrahedron
Volume65
Issue number4
DOIs
Publication statusPublished - 2009 Jan 24

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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