Asymmetric synthesis of (+)-hirsutene

…, S Venkataraman, RA Ostrander, GZ Sinai…

Index: Hua, Duy H.; Venkataraman, S.; Ostrander, Robert A.; Sinai, Gurudas-Z.; McCann, Peggy J.; et al. Journal of Organic Chemistry, 1988 , vol. 53, # 3 p. 507 - 515

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Citation Number: 49

Abstract

The asymmetric total synthesis of (+)-hirsutene from the regio-and enantioselective 1, 4-y- addition reaction of (-)-(S)-allyl p-tolyl sulfoxide and 2-methyl-2-cyclopentenone is presented. In this total synthesis, a facile ring closure reaction involving enol thioether and enol acetate moieties and the deoxygenation reaction of a highly hindered secondary alcohol via its 2-propanesulfonate were found. An unexpected displacement reaction at ...