Formal synthesis of salinosporamide a starting from D-glucose

Takayuki Momose, Yuji Kaiya, Jun Ichi Hasegawa, Takaaki Sato, Noritaka Chida

研究成果: Article査読

34 被引用数 (Scopus)

抄録

A formal synthesis of salinosporamide A is described. The tertiary alcohol function in salinosporamide A was stereoselectively generated via the substrate control by the reaction of a cyclic ketone derived from D-glucose with Me3Al, and subsequent Overman rearrangement of an allylic trichloroacetimidate effectively constructed the tetrasubstituted carbon with nitrogen. Formation of g-lactam, followed by the introduction of a cyclohexenyl unit furnished the Corey's intermediate of salinosporamide A.

本文言語English
ページ(範囲)2983-2991
ページ数9
ジャーナルSynthesis
17
DOI
出版ステータスPublished - 2009

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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