Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
α-, β-, and γ-Irones and analogues have been prepared from optically active ketones (+)-1, (+)-6a,b, and (+)-17, via a Corey-Chaykovsky oxiranylation (Me2S, Me2SO4, Me2SO, NaOH) followed by isomerisation (SnCl4 or MgBr2). (+)-Dihydrocyclocitral (19a), obtained from (-)-citronellal, and analogue (+)-19b, were condensed with various ketones to afford (+)-21a-f, and after hydrogenation (+)-22a-f. A mild oxidative degradation of aldehydes (+)-trans-and (-)-cis-8a,b, to ketones (-)-16a,b, as well as olfactive evaluations, 13C-NMR assignments, and absolute configurations of the intermediate epoxides, aldehydes, and alcohols are presented.
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