STEREOSELECTIVE SYNTHESIS OF (4S,5R,6S)-4-(5,6-EPOXY-6-PHENYL)-GAMMA-LACTONE

Authors
SOLLADIECAVALLO A ROCHE D BOLD G ACEMOGLU F TINTELNOTBLOMLEY M FISCHER J DECIAN A
Citation
A. Solladiecavallo et al., STEREOSELECTIVE SYNTHESIS OF (4S,5R,6S)-4-(5,6-EPOXY-6-PHENYL)-GAMMA-LACTONE, Tetrahedron : asymmetry, 7(6), 1996, pp. 1797-1810
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
6
Year of publication
1996
Pages
1797 - 1810
Database
ISI
SICI code
0957-4166(1996)7:6<1797:SSO(>2.0.ZU;2-X
Abstract
A short (7 steps) and efficient (45% overall yield) synthesis of (4S,5 R,6S)-4-(5,6-epoxy-6-phenyl)-gamma-lactone, a versatile intermediate t oward possible HIV-1 protease inhibitors, is described. Two examples o f trans-alpha-benzylation of the lactonic ring followed by a regiosele ctive opening of the epoxide (with thiopropanamide) as well as an open ing of the lactone ring with L-valine (2-methoxy-ethyl)-amide are also given. Copyright (C) 1996 Elsevier Science Ltd