In the quest for a virtual pseudo receptor for sandalwood-like odorants. Part I: The empirical approach.
Based on similarities between naturally occurring (-)-(Z)-beta- or (+)-(Z)-alpha-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.
Chapuis
Christian
C
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D036262:Empirical Research; D009812:Odorants / Q000032:analysis*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification; D010938:Plant Oils / Q000737:chemistry / Q000302:isolation & purification*; D010940:Plant Proteins / Q000737:chemistry / Q000302:isolation & purification*; D000081223:Polycyclic Sesquiterpenes; D032123:Santalum; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification
D010936:Plant Extracts; D010938:Plant Oils; D010940:Plant Proteins; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C043206:santalol