Serendipitous synthesis and configurational assignment of (-)-Gabosine J

Tony K.M. Shing, Y. Chen, Ho T. Wu

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

2-epi-Gabosine I, unambiguously synthesized from benzyl d-mannopyranoside in nine steps with 34% overall yield, has been shown to be identical to gabosine J by NMR spectral analysis, thereby indicating that the relative stereochemistry of gabosine J was incorrectly determined formerly as a syn-triol. The relative and absolute configurations of (-)-gabosine J are now revised and confirmed as (2S,3S,4R)-trihydroxy-5-hydroxymethylcyclohex-5-en-1- one. Since the specific rotation of the natural product has not been recorded, the absolute configuration of natural gabosine J is either (-)-gabosine J or its enantiomer.

Original languageEnglish
Pages (from-to)1793-1796
Number of pages4
JournalSynlett
Volume23
Issue number12
DOIs
Publication statusPublished - 2012 Jul 4

Keywords

  • Wittig reaction
  • carbohydrates
  • enones
  • natural products
  • stereoselective synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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