Radical cyclization of some unsaturated carbohydrate-derived propargyl ethers and acetals
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 999-1007
- https://doi.org/10.1039/p19920000999
Abstract
Treatment of propargyl ethers and acetals derived from deoxy-D-hexenopyranosides of erythro and threo configuration with tributyltin hydride with a radical initiator gave fused pyranofuranosides. This vinylic radical cyclization allowed the completely stereo- and regio-specific introduction, at the C-2 or C-3 position, of a functionalized carbon chain which can be further manipulated to create new chiral centres.Keywords
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