Enantioselective approach to 7-azabicyclo[2.2.1]heptane ring systems using D-(−)-quinic acid as the chiral educt: Application to the formal synthesis of (+)-epibatidine

By utilizing D-(−)-quinic acid as the chiral starting material the optically pure 7-[(1,1-dimethylethoxy)carbonyl]-7-azabicyclo[2.2.1.]heptan-2-one 2, an advanced intermediate already taken to (+)-epibatidine 1, a non-opioid analgesic isolated from Ecuadorian poison frogs, was synthetized through a...

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Bibliographic Details
Published in:Tetrahedron letters 1997, Vol.38 (4), p.681-684
Main Authors: Albertini, Enrichetta, Barco, Achille, Benetti, Simonetta, De Risi, Carmela, Pollini, Gian P., Zanirato, Vinicio
Format: Article
Language:English
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Summary:By utilizing D-(−)-quinic acid as the chiral starting material the optically pure 7-[(1,1-dimethylethoxy)carbonyl]-7-azabicyclo[2.2.1.]heptan-2-one 2, an advanced intermediate already taken to (+)-epibatidine 1, a non-opioid analgesic isolated from Ecuadorian poison frogs, was synthetized through a facile, regioselective intramolecular nucleophilic ring opening of a cyclic sulfate moiety. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(96)02391-X