𝔖 Bobbio Scriptorium
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Configuration-Odor Relationships in 5β-Ambrox

✍ Scribed by Sina Escher; Wolfgang Giersch; Yvan Niclass; Gérald Bernardinelli; Günther Ohloff

Book ID
102858297
Publisher
John Wiley and Sons
Year
1990
Tongue
German
Weight
731 KB
Volume
73
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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.

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