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. 2005 Jan 21;3(2):340-7.
doi: 10.1039/b413817c. Epub 2004 Dec 16.

Tandem cyclisations involving alpha-ketenyl alkyl radicals. New syntheses of the natural triquinanes pentalenene and modhephene

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Tandem cyclisations involving alpha-ketenyl alkyl radicals. New syntheses of the natural triquinanes pentalenene and modhephene

Benoît De Boeck et al. Org Biomol Chem. .

Abstract

New synthetic approaches to the angular and propellane sesquiterpene triquinanes (+/-)-pentalenene 2 and (+/-)-modhephene 3, respectively, are described. The syntheses are based on tandem cyclisations involving alpha-ketene alkyl radical intermediates produced from alpha,beta-unsaturated acyl radical species, as highlighted in Schemes 2 and 4.

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