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Syntheses of the Enantiomers of Vulcanolide ®
Author(s) -
Fehr Charles,
ChaptalGradoz Nathalie
Publication year - 2002
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 - 10.1002/1522-2675(200202)85:2<533::aid-hlca533>3.0.co;2-5
Subject(s) - chemistry , enantiomer , stereocenter , resolution (logic) , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , artificial intelligence , computer science
The synthesis of the enantiomers of Vulcanolide ® ((±)‐ 7 ) is described, the strongest musk odorant among hundreds of structurally related analogues, by resolution of an intermediate. To this end, we devised a new route which involves the temporary introduction of a modulable functional group in the vicinity of the stereogenic centers ( Scheme 2 ). The resolution is based on the chromatographic separation of two diastereoisomeric camphanic acid esters. The strong and characteristic note of racemic Vulcanolide ® is almost entirely due to the (−)‐enantiomer. This synthesis has allowed the preparation of new, structurally related musk odorants.