Transformation of. alpha.-and. beta.-ionones into. alpha.-and. beta.-damascone and. beta.-damascenone using allylsilane chemistry

…, C Faggi, N Gelsomini, M Taddei

Index: Azzari, Elisabetta; Faggi, Cristina; Gelsomini, Nedo; Taddei, Maurizio Journal of Organic Chemistry, 1990 , vol. 55, # 3 p. 1106 - 1108

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Citation Number: 12

Abstract

The transformation of a-ionone (1) into a-damascone (7) was achieved in 22% overall yield6 and did not affect the chiral center present in the starting material, 7 giving 7 in optically pure form ([aImD=+ 330 (c= 10 in CHCl,)[lit. 7b [aJ20D=+ 324'(c= 10 in CHCI,)]. p-Damascone (13) and 0-damascenone (14) were analogously prepared from@-ionone (8) via allylsilane 11. Treatment of 11 with MCPBA followed by TBAF gave@-damascol 12 in 55% yield (see ...