CONVENIENT DIASTEREOSPECIFIC SYNTHESIS OF A ROCIVERINE PRECURSOR AND ITS RESOLUTION BY LIPASE-CATALYZED TRANSESTERIFICATION

Authors
DIBUSSOLO V CATELANI G MASTRORILLI E DIBUGNO C GIORGI R
Citation
V. Dibussolo et al., CONVENIENT DIASTEREOSPECIFIC SYNTHESIS OF A ROCIVERINE PRECURSOR AND ITS RESOLUTION BY LIPASE-CATALYZED TRANSESTERIFICATION, Tetrahedron : asymmetry, 7(12), 1996, pp. 3585-3592
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
12
Year of publication
1996
Pages
3585 - 3592
Database
ISI
SICI code
0957-4166(1996)7:12<3585:CDSOAR>2.0.ZU;2-T
Abstract
-)-1-Cyclohexyl-c-2-hydroxymethyl-r-1-cyclohexanol 3, a precursor of t he antimuscarinic drug Rociverine 1, was obtained diastereospecificall y in very high yield, from the Grignard reaction between C6H11MgCl and an appropriately protected 2-(hydroxymethyl)cyclohexanone. The prepar ation of enantiomerically enriched cis diol(+)-(1R,2S)-3 and the corre sponding 2-acetoxymethyl derivative (+)-(1S,2R)-12 was achieved by lip ase PPL-catalyzed transesterification of racemic diol (+/-)-3. Copyrig ht (C) 1996 Elsevier Science Ltd.