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Structure-odor correlation, XXIV: Synthesis and olfactory properties of damascene and damascenone analogs
Weyerstahl, Peter,Licha, Kai
, p. 809 - 814 (2007/10/03)
The aldehydes rac-1, rac-2, and 3 were conveniently prepared by starting from isophorone (4). Reaction of 1-3 with (E,Z)-1-bromo-1-propene (14) afforded the rac-allylic alcohols (E,Z)-15, -18, and -20. The alcohols were oxidized to the damascone/damascenone analogs 1-(3,5,5-trimethyl-2-cyclohexen-1-yl)- (rac-16), 1-(3,5,5-trimethyl-1-cyclohexen-1-yl)-(rac-19), and 1-(3,5,5-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one (21), and the (E/Z) isomers were separated by FC. Their olfactory evaluation shows that the highly estimated odor of damascone (A, B) and damascenone (C) is more or less lost. This result can be explained by force-field calculation of the lowest energy conformation of 16, 19, and 21 in comparison with those of A-C. VCH Verlagsgesellschaft mbH, 1996.
