Alkylation of enolate ions generated regiospecifically via organocopper reactions. Synthesis of decalin sesquiterpene valerane and of prostaglandin model systems

GH Posner, J Sterling, CE Whitten…

Index: Posner,G.H. et al. Journal of the American Chemical Society, 1975 , vol. 97, # 1 p. 107 - 118

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Citation Number: 117

Abstract

Abstract: Results are reported on alkylation reactions of four different structural types of cycloalkanone enolate ions (1-4) each of which is generated regiospecifically via an organocopper reaction with an ol, a'-dibromo ketone or with a 2-cycloalkenone. These results provide information on the relative rates of enolate alkylation vs. equilibration in these systems, and they have led to a new total synthesis of the decalin sesquiterpene ...