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Synthesis and odour evaluation of stereoisomers of octahydrobenzopyran derivatives
Author(s) -
LinaresPalomino Pablo J.,
Salido Sofía,
Altarejos Joaquín,
Nogueras Manuel,
Sánchez Adolfo
Publication year - 2006
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.1643
Subject(s) - ionone , chemistry , yield (engineering) , stereochemistry , bicyclic molecule , benzopyran , organic chemistry , metallurgy , materials science
The synthesis and isolation of the four racemic 2,5,5,8a‐tetramethyl‐3,4,4a,5,6,7,8,8a‐octahydro‐2 H ‐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.