Pablo J. Linares-Palomino, S. Salido, J. Altarejos
Jul 1, 2006
Citations
0
Influential Citations
9
Citations
Journal
Flavour and Fragrance Journal
Abstract
The synthesis and isolation of the four racemic 2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-2H-1-benzopyran stereoisomers from β-ionone and α-ionone is reported. It was based on the cyclization of dihydro-β-ionone and dihydro-α-ionone with chlorosulfonic acid at low temperature to yield stereospecifically the trans-fused and cis-fused hexahydrobenzopyran derivatives, respectively. The direct cyclization of dihydro-β-ionol and dihydro-α-ionol under identical conditions was also explored. In addition to the complete spectroscopic characterization of every isolated isomer, a description of their olfactory properties is displayed. Copyright © 2006 John Wiley & Sons, Ltd.