Facile regio- and stereo-specific allylic oxidation of gem-dimethyl olefins via addition of benzenesulphenyl chloride. Synthesis of allylic oxygenated terpenes
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1289-1295
- https://doi.org/10.1039/p19840001289
Abstract
Novel and facile terminal trans-allylic and internal allylic oxidations of the gem-dimethyl olefin terminus of the terpenoids (1) are described which take place site-, regio-, and stereo-specificially via the same intermediate adduct between benzenesulphenyl chloride and (1). By this method, the allylic oxygenated terpenes (±)-nuciferal (11), (±)-ar-turmerone (12), (±)-ipsdienol (3c), neotorreyol (2e), (±)-6-hydroxydendrolasin (3e), and 6-oxodendrolasin (14) were synthesized.This publication has 6 references indexed in Scilit:
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