Intramolecular additions of allylsilanes to conjugated dienones. The synthesis of three perforanes

G Majetich, J Defauw, C Ringold

Index: Majetich, George; Defauw, Jean; Ringold, Clay Journal of Organic Chemistry, 1988 , vol. 53, # 1 p. 50 - 68

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Citation Number: 55

Abstract

Intramolecular addition of allylsilanes to 3-vinylcycloalkenones provides a powerful means of constructing functionalized 5-5, 5-7, 6-5, and 6-7 bicyclic ring systems. Our results reveal a divergence in reactivity, dependent on reaction catalyst and substrate structure, which can be explained in terms of conformational and stereoelectronic effects. The synthesis of three perforanes is also presented.