✍ Scribed by Charles Fehr; Nathalie Chaptal-Gradoz
No coin nor oath required. For personal study only.
The synthesis of the enantiomers of Vulcanolide ¾ ((AE)-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 ¾ is almost entirely due to the (À)-enantiomer. This synthesis has allowed the preparation of new, structurally related musk odorants.
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