Regiocontrolled synthesis of mono-, di-, and trisubstituted cyclohexenones by cycloaddition of vinyl sulfones to 1-methoxy-3-[(trimethylsilyl) oxy]-1, 3-butadienes. …

…, GD Crouse, LA Paquette

Index: Kinney, William A.; Crouse, Gary D.; Paquette, Leo A. Journal of Organic Chemistry, 1983 , vol. 48, # 25 p. 4986 - 5000

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Citation Number: 51

Abstract

Cycloaddition of phenyl vinyl sulfone to Danishefsky's diene followed by direct ketalization provided 7, a synthon for the 4-(2-cyclohexenyl) anion. Thus, 7 readily undergoes regiospecific y-alkylation. Ensuing reductive desulfonylation and hydrolysis provides 2-(and 3-) cyclohexenones efficiently. Zingiberenol, a monocyclic ses-quiterpene, was prepared by means of this methodology. Terminal alkenes and cyclic olefins enter into comparable ...