Stereoselective synthesis and relative configuration assignment of gabosine J

J Org Chem. 2012 Jun 1;77(11):5030-5. doi: 10.1021/jo300456q. Epub 2012 May 23.

Abstract

The first total synthesis of (+)-gabosine J and that of the epimer at C4 of its enantiomer have been accomplished through an enantioselective approach from a common intermediate 1. These syntheses have allowed us to establish the correct relative configuration of the natural metabolite, which was originally misassigned. This work, together with our former syntheses of other gabosines and related compounds, validates enone 1 as a general synthetic precursor for this kind of carbasugars.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclohexanones / chemical synthesis*
  • Cyclohexanones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Stereoisomerism

Substances

  • Cyclohexanones
  • gabosine J