Intramolecular direct Aldol reactions of sugar diketones: Syntheses of valiolamine and validoxylamine G

Tony K.M. Shing, Hau M. Cheng

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27 Citations (Scopus)

Abstract

(Chemical Equation Presented) A new and stereoselective intramolecular direct aldol reaction of diketones derived from carbohydrates has been developed to construct carbocycles with D-gluco-, D-galacto, D-manno-, and L-ido-configurations. The stereochemical outcome of the aldol reaction of the diketone is dependent on the base used. Transformation of D-gluco-aldols readily affords valiolamine which also constitutes a formal synthesis of voglibose. Facile conversion of D-gluco-cyclohexanones into validoxylamine G has been achieved in 12 steps with 15.1% overall yield from D-glucose.

Original languageEnglish
Pages (from-to)4137-4139
Number of pages3
JournalOrganic Letters
Volume10
Issue number18
DOIs
Publication statusPublished - 2008 Dec 1

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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