Total syntheses of (+)- and (–)-nonactate esters using silicon compounds to control the stereochemistry
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 19,p. 2285-2286
- https://doi.org/10.1039/c39940002285
Abstract
1,3-Transposition, using the epoxidation of the allylsilane 7, derived from the meso 3,4-disilylated adipate 1, gives the 1,4-related stereocentres of 8-oxo-6-hydroxy-3-dimethyl(tolyl)silylnonanoic acid ethylene acetal 10; two highly stereocontrolled sequences from this common intermediate give methyl (+)-nonactate 13 and benzyl (–)-nonactate 17.Keywords
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