LIPASE-CATALYZED ASYMMETRIC DEMETHOXYCARBONYLATION - FORMAL SYNTHESESOF (-CARBACYCLIN, (-)-AJMALICINE, AND (-)-TETRAHYDROALSTONINE())

Authors
NODE M INOUE T ARAKI M NAKAMURA D NISHIDE K
Citation
M. Node et al., LIPASE-CATALYZED ASYMMETRIC DEMETHOXYCARBONYLATION - FORMAL SYNTHESESOF (-CARBACYCLIN, (-)-AJMALICINE, AND (-)-TETRAHYDROALSTONINE()), Tetrahedron : asymmetry, 9(1), 1998, pp. 157-167
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
1
Year of publication
1998
Pages
157 - 167
Database
ISI
SICI code
0957-4166(1998)9:1<157:LAD-FS>2.0.ZU;2-O
Abstract
Both enantiomers of C-2-symmetric dimethyl 3,7-dihydroxybicyclo[3.3.0] -octa-2,6-dicarboxylate 3 were prepared in enantiomerically pure form from symmetric tetraester 1 by the lipase-catalyzed demethoxycarbonyla tion, respectively. Double asymmetric differentiation with lipase in t he above demethoxycarbonylation was observed. Their applications to fo rmal total syntheses of (+)-carbacyclin and (-)-ajmalicine including ( -)-tetrahydroalstonine are also described. (C) 1998 Elsevier Science L td. All rights reserved.