Lipase-mediated resolution of octahydro-3,3,8a-trimethyl-naphthalenol, a key intermediate in the total synthesis of lactaranes and marasmanes

Authors
Franssen, MCR Jongejan, H Kooijman, H Spek, AL Bell, RPL Wijnberg, JBPA de Groot, A
Citation
Mcr. Franssen et al., Lipase-mediated resolution of octahydro-3,3,8a-trimethyl-naphthalenol, a key intermediate in the total synthesis of lactaranes and marasmanes, TETRAHEDR-A, 10(14), 1999, pp. 2729-2738
Citations number
51
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
14
Year of publication
1999
Pages
2729 - 2738
Database
ISI
SICI code
0957-4166(19990716)10:14<2729:LROOAK>2.0.ZU;2-1
Abstract
The bicyclic alcohol(1 alpha,8a alpha)-1,2,3,4,6,7,8,8a-octahydro-3,3,8a-tr imethyl-1-naphthalenol (+/-)-1 was resolved using Candida rugosa lipase-med iated esterification with vinyl acetate (E=72). The absolute configuration of the remaining isomer was determined by X-ray analysis of its 4-chloro-3- nitrobenzoate. The observed stereochemical preference of the enzyme is in l ine with the rule formulated by Kazlauskas et al. [Kazlauskas, R. J.; Weiss floch, A. N. E.; Rappaport, A. T; Cuccia, L. A. J. Org. Chem. 1991, 56, 265 6-2665]. The resolved alcohol is a useful chiral synthon for natural lactar ane and marasmane sesquiterpenes. (C) 1999 Elsevier Science Ltd. All rights reserved.