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

Nobuyuki Hayashi, Takahiro Suzuki, Kenji Usui, Masahisa Nakada*

*この研究の対応する著者

研究成果: Article査読

16 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)888-895
ページ数8
ジャーナルTetrahedron
65
4
DOI
出版ステータスPublished - 2009 1 24

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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