Abstract
An efficient conversion of allyl sulfide 6 prepared
from (-)-quinic acid (5) to gabosines
was achieved by a series of sequential reactions: i) Mislow-Evans
rearrangement, ii) SeO2 oxidation, iii) conjugate addition
of sodium hydroxide or sodium acetate, and iv) elimination of the
methoxymethyloxy group.
Key words
gabosine - cyclitol - allyl sulfide - quinic
acid - conjugate addition
References
Isolation and biological activity
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The allyl sulfide can
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Yields on the deprotection step to
gabosines were good to moderate (>59%) due probably
to the prolonged reaction period leading to the undesired acid-catalyzed decomposition.
