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

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 radica...

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Veröffentlicht in:	Organic & biomolecular chemistry 2005-01, Vol.3 (2), p.340-347
Hauptverfasser:	De Boeck, Benoît, Harrington-Frost, Nicole M, Pattenden, Gerald
Format:	Artikel
Sprache:	eng
Schlagworte:	Bridged-Ring Compounds - chemical synthesis Bridged-Ring Compounds - chemistry Cyclization Cyclopentanes - chemical synthesis Cyclopentanes - chemistry Ethylenes - chemistry Free Radicals - chemical synthesis Free Radicals - chemistry Ketones - chemistry Molecular Conformation Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Stereoisomerism
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Zusammenfassung:	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.
ISSN:	1477-0520 1477-0539
DOI:	10.1039/b413817c