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Configuration‐Odor Relationships in 5β‐Ambrox
Author(s) -
Escher Sina,
Giersch Wolfgang,
Niclass Yvan,
Bernardinelli Gérald,
Ohloff Günther
Publication year - 1990
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.19900730717
Subject(s) - odor , chemistry , furan , diastereomer , stereochemistry , organic chemistry
The four possible A/B cis ‐fused diastereoisomers of Ambrox ® have been synthesized and their configurations and conformations established by X‐ray and NMR analysis. Only 5β‐ambrox (= 1,2,3a,4,5,5β,6,7,8,9,9a,9bα‐dodecahydro‐3aβ,6,6,9aβ‐tetramethylnaphtho[2,1‐ b ]furan; 5 ) has an odor quality comparable to Ambrox ®. The 1,3‐synperiplanar/diaxial conformation of the substituents at C(8) ( = C(3a)) and C(10) (= C(9a)) has thus been confirmed to be a compulsory structure element for the particular odor.