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Preparation of Campholenal Analogues: Chirons for the lipophilic moiety of sandalwood‐like odorant alcohols
Author(s) -
Chapuis Christian,
Brauchli Robert
Publication year - 1992
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.19920750507
Subject(s) - chemistry , intramolecular force , moiety , ring (chemistry) , sandalwood , aldol condensation , isomerization , stereochemistry , aldol reaction , ozonolysis , organic chemistry , catalysis , archaeology , history
In connection with structure‐activity relationship studies, analogues of campholenal ((+)‐ 4b ), an important building block for sandalwood‐like odorants, were prepared. The five‐membered‐ring analogues 4 were obtained by epoxidation of the corresponding α‐pinene derivatives 2 , followed by catalytic ZnBr 2 isomerisation ( Scheme 2 ). The six‐membered‐ring skeleton was obtained by ozonolysis of α‐campholenyl acetate ((−)‐ 14b ), followed by intramolecular aldol condensation ( Scheme 5 ). 13 C‐NMR assignments are given.