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
Full Text: HTML
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 ...
Related Articles:
Interchange of functionality in conjugated carbonyl compounds through isoxazoles
[Journal of the American Chemical Society, , vol. 94, p. 9128 - 9132]
TBAF-Triggered Aldol-Type Addition of α-Triethylsilyl-α-diazoacetone
[Pellicciari, Roberto; Fringuelli, Renata; Sisani, Ettore; Curini, Massimo Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981 , p. 2566 - 2569]
Synthetic studies on damascenones
[Helvetica Chimica Acta, , vol. 54, p. 1767 - 1775]
A new synthesis of. alpha.-and. beta.-damascones from the ionones.
[Journal of Organic Chemistry, , vol. 57, # 9 p. 2757 - 2760]
[Journal of Organic Chemistry, , vol. 55, # 3 p. 1106 - 1108]