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 language | English |
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Pages (from-to) | 1793-1796 |
Number of pages | 4 |
Journal | Synlett |
Volume | 23 |
Issue number | 12 |
DOIs | |
Publication status | Published - 2012 Jul 4 |
Keywords
- Wittig reaction
- carbohydrates
- enones
- natural products
- stereoselective synthesis
ASJC Scopus subject areas
- Organic Chemistry