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

…, NM Harrington-Frost, G Pattenden

Index: De Boeck, Benoit; Harrington-Frost, Nicole M.; Pattenden, Gerald Organic and Biomolecular Chemistry, 2005 , vol. 3, # 2 p. 340 - 347

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Citation Number: 35

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 α-ketene alkyl radical intermediates produced from α, β-unsaturated acyl radical species, as highlighted in Schemes 2 and 4.