The development of a facile tandem Wolff/Cope rearrangement for the synthesis of fused carbocyclic skeletons

R Sarpong, JT Su, BM Stoltz

Index: Sarpong, Richmond; Su, Julius T.; Stoltz, Brian M. Journal of the American Chemical Society, 2003 , vol. 125, # 45 p. 13624 - 13625

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Citation Number: 50

Abstract

A set of mild processes for the conversion of vinyl cyclopropyl diazo ketones to highly functionalized cycloheptadienones and vinyl cyclopentenones by use of a target-inspired tandem Wolff/Cope rearrangement sequence is described. A divergent reaction course of the vinyl cyclopropyl diazo ketone substrates under sono-or photochemical activation provides good to excellent yields (55-98%) of the product cycloheptadienones and vinyl ...