Enantiospecific total synthesis of both enantiomers of laurene by a chemical diastereoselection/lipase-catalyzed kinetic resolution sequence

Authors
Laval, G Audran, G Sanchez, S Monti, H
Citation
G. Laval et al., Enantiospecific total synthesis of both enantiomers of laurene by a chemical diastereoselection/lipase-catalyzed kinetic resolution sequence, TETRAHEDR-A, 10(10), 1999, pp. 1927-1933
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
10
Year of publication
1999
Pages
1927 - 1933
Database
ISI
SICI code
0957-4166(19990521)10:10<1927:ETSOBE>2.0.ZU;2-D
Abstract
A short and efficient enantiospecific total synthesis of natural (+)-lauren e and its enantiomer is described. The methodology was developed by employi ng a stereoselective H-ene reaction of an isocyclic allyltrimethylsilane wi th paraformaldehyde, followed by a lipase-mediated kinetic resolution of th e racemic key intermediate. (C) 1999 Elsevier Science Ltd. All rights reser ved.