Configuration‐Odor Relationships in 5β‐Ambrox | Zendy

Escher Sina | Zendy; Giersch Wolfgang | Zendy; Niclass Yvan | Zendy; Bernardinelli Gérald | Zendy; Ohloff Günther | Zendy

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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.

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