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

Tony Kung Ming 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
Externally publishedYes

Fingerprint

Stereochemistry
Enantiomers
Mannose
Biological Products
Spectrum analysis
Nuclear magnetic resonance
gabosine J
gabosine I

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Serendipitous synthesis and configurational assignment of (-)-Gabosine J. / Shing, Tony Kung Ming; Chen, Y.; Wu, Ho T.

In: Synlett, Vol. 23, No. 12, 04.07.2012, p. 1793-1796.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Chen, Y. ; Wu, Ho T. / Serendipitous synthesis and configurational assignment of (-)-Gabosine J. In: Synlett. 2012 ; Vol. 23, No. 12. pp. 1793-1796.
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