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

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

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)


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
Issue number12
Publication statusPublished - 2012 Jul 4


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

ASJC Scopus subject areas

  • Organic Chemistry


Dive into the research topics of 'Serendipitous synthesis and configurational assignment of (-)-Gabosine J'. Together they form a unique fingerprint.

Cite this