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

Authors
Node, M Nakamura, S Nakamura, D Katoh, T Nishide, K
Citation
M. Node et al., 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, TETRAHEDR L, 40(29), 1999, pp. 5357-5360
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
29
Year of publication
1999
Pages
5357 - 5360
Database
ISI
SICI code
0040-4039(19990716)40:29<5357:NADO3>2.0.ZU;2-2
Abstract
The porcine liver esterase-catalyzed dealkoxycarbonylation of 8-benzyl-3-ox o-8-azabicyclo[3.2.1]octane-2,4-dicarboxylates (4) was found to give high e nantiomeric excess of the desymmetrized keto ester (5). This novel dealkoxy lcarbonylation opened a new route to the asymmetric synthesis of (1R)cocain e related radiopharmaceuticals such as (1R)-beta-CIT, for diagnosis of Park inson's disease. (C) 1999 Elsevier Science Ltd. All rights reserved.