Formal synthesis of salinosporamide a starting from D-glucose

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

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2983-2991
Number of pages9
JournalSynthesis
Issue number17
DOIs
Publication statusPublished - 2009

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Ketones
Glucose
Alcohols
Nitrogen
Carbon
Substrates
Lactams
marizomib

Keywords

  • Carbohydrates
  • Chiral pool
  • Pericyclic reactions
  • Rearrangements
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

Cite this

Formal synthesis of salinosporamide a starting from D-glucose. / Momose, Takayuki; Kaiya, Yuji; Hasegawa, Jun Ichi; Satou, Takaaki; Chida, Noritaka.

In: Synthesis, No. 17, 2009, p. 2983-2991.

Research output: Contribution to journalArticle

Momose, Takayuki ; Kaiya, Yuji ; Hasegawa, Jun Ichi ; Satou, Takaaki ; Chida, Noritaka. / Formal synthesis of salinosporamide a starting from D-glucose. In: Synthesis. 2009 ; No. 17. pp. 2983-2991.
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