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In the Quest for a Virtual Pseudo Receptor for Sandalwood‐Like Odorants. Part I
Author(s) -
Chapuis Christian
Publication year - 2004
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200490084
Subject(s) - chemistry , sandalwood , substituent , imperfect , function (biology) , vicinal , stereochemistry , alkyl , evolutionary biology , organic chemistry , philosophy , linguistics , theology , biology
Based on similarities between naturally occurring (−)‐( Z )‐ β ‐ or (+)‐( Z )‐ α ‐santalol ((−)‐ 1 or (+)‐ 2 , resp.) and the reversed ( E )‐configured synthetic derivatives from campholenal ( 7a ), a simple model A was developed. Besides reconciliation of this stereochemical aspect, this initial model also tentatively explained the enantiodiscriminations as well as the large spectra of distances separating the OH function from the lipophilic quaternary center(s) reported for different classes of substrates. Evolution, modifications, and refinement of this imperfect model allied with the research for alternative possibilities are illustrated, along with a historical guideline, in the light of olfactively challenging synthetic seco‐substructures as well as literature reports. Despite evolution of the inadequate model A and a plausible interpretation of the lipophilic part, the topological positions of the OH function and its vicinal alkyl substituent could nevertheless not be fully ascertained by this approach. This apparently inconclusive empirical concept prompted us to turn our attention towards a computerized methodology, which will constitute the second and third part of this study.