A Method for Direct Alkylation of 1,4aβ-Dimethyl-5β-Hydroxy-4,4a,5,6,7,8-Hexahydronaphthalen-2 (3H)-ONE

Abstract

Octalones of the type 1 are useful synthons for terpenoids andsteroids. Often, synthetic transformations such as alkylation¹ of these ketols require prior protection of the hydroxy function due to propensity of such δ - hydroxy- α-enones to undergo facile vinylogous retrogradealdol reactions² as shown in structure 2. Thus, attempted meythylation, as well as preparation of o-benzyl derivatives of the parent octalone (1a) have been reported^1a,be to be unsuccessful due to above said fragmentation.