Carbocyclization of d-glucose: Syntheses of gabosine i and streptol

Tony K.M. Shing, Y. Chen, Wai Lung Ng

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

d-Glucose was differentially protected with a trans-diacetal at C-2,3, an ethoxymethyl ether at C-4, and a tert-butyldimethylsilyl ether at C-6, and then carbocyclized via a key Horner-Wadsworth-Emmons (HWE) olefination to give a versatile synthetic intermediate, enone 13, which was readily transformed into gabosine I and streptol.

Original languageEnglish
Pages (from-to)6001-6005
Number of pages5
JournalTetrahedron
Volume67
Issue number33
DOIs
Publication statusPublished - 2011 Aug 19

Keywords

  • Carbohydrate
  • Natural products
  • Synthesis
  • Wittig reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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