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Zur Stereochemie der Geruchswahrnehmung von 1‐Dekalon‐Derivaten und ihren oxaanalogen Verbindungen
Author(s) -
Ohloff Günther,
Giersch Wolfgang,
SchulteElte Karl H.,
Vial Christian
Publication year - 1976
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.19760590418
Subject(s) - chemistry , odor , labdane , stereochemistry , terpenoid , organic chemistry
Stereochemistry‐odor relationships in the 1‐decalone series and their oxa‐analogs. The olfactory relationships of (−)‐(9 S ,10 S )‐5,5,9‐trimethyl‐ trans ‐1‐decalone ( 2a ), 6 diasterioisomers in the 11‐nordriman‐9‐one series ( 2b ‐ g ), and 20 racemic 2‐oxabicyclo[4.4.0]decanes are reported and correlated with the ‘Triaxial Rule of Odor Sensation’. This rule also is applied to the two internal C(13) acetals derived from (±)‐dihydro‐γ‐ionone as well as to two epimeric C(18) ethers in the labdane series. Syntheses are described for most of the compounds examined.