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An expedient preparation of enantio‐enriched ambergris odorants starting from commercial ionone alpha
Author(s) -
Serra Stefano
Publication year - 2013
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.3126
Subject(s) - ionone , chemistry , enantioselective synthesis , stereochemistry , odor , block (permutation group theory) , organic chemistry , catalysis , geometry , mathematics
We report the enantioselective synthesis of the ambergris odorants (+)‐( S )‐ γ ‐ionone, (+)‐( S )‐ γ ‐dihydroionone, (−)‐ α ‐ambrinol, (+)‐( S )‐ γ ‐coronal, (−)‐( S )‐ γ ‐homocyclogeranyl chloride and (+)‐( S )‐ γ ‐homocyclogeraniol. At first, the enantio‐enriched (4 R ,6 S )‐4‐acetoxy‐ γ ‐ionone was prepared starting from commercial racemic ionone alpha by means of a chemo‐enzymatic process. This chiral building block was then converted into ( S )‐ γ ‐dihydroionone which was used as the starting material for the synthesis of the aforementioned odorants. Copyright © 2012 John Wiley & Sons, Ltd.