Premium
Synthetic Studies on Damascenones
Author(s) -
Büchi G.,
Wüest H.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540704
Subject(s) - chemistry , isomerization , ethyl acetoacetate , lithium (medication) , alkoxide , organic chemistry , ethyl chloride , chloride , odor , propenyl , acetyl chloride , medicinal chemistry , catalysis , medicine , endocrinology
The odor principle β‐damascenone and its isomer α‐damascenone have been prepared by treatment of the corresponding ethyl safranates with excess allyl lithium followed by alkoxide catalyzed isomerization of the resulting products with β, γ‐unsaturated ketonic side chains. Addition of allyltriphenylphosphorane (preferably prepared from allyltriphenylphosphonium chloride) rather than the propenyl isomer to ethyl α‐isopropylidene‐acetoacetate produced ethyl α‐safranate. This represents a new, potentially general method for the synthesis of functionalized cyclohexadienes.