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ChemInform Abstract: Novel Asymmetric Dealkoxycarbonylation of 3-Oxo-8-azabicyclo[3.2.1]octane-2,4-dicarboxylates Using Porcine Liver Esterase: A New Route to (-)-Anhydroecgonine Methyl Ester.

✍ Scribed by Manabu Node; Soichi Nakamura; Daisaku Nakamura; Takahiro Katoh; Kiyoharu Nishide


Publisher
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis


Novel Asymmetric Dealkoxycarbonylation of 3-Oxo-8azabicyclo[3.2.1]octane-2,4-dicarboxylates Using Porcine Liver Esterase: A New Route to (-)-Anhydroecgonine Methyl Ester. -PLE-Catalyzed dealkoxycarbonylation of the bicyclic diesters of type (I) can give the corresponding desymmetrized keto esters in high enantiomeric excess. Compound (II) serves as starting material for a novel route to the (-)-cocaine derived anhydroecgonine (III), which is a valuable precursor of the radiodiagnostics (1R)-β-CIT and (1R)-β-CFT. -(NODE, MANABU;