Tetrahedron Asymmetry p. 1797 - 1810 (1996)
Update date:2022-08-03
Topics:
Solladie-Cavallo, Arlette
Roche, Didier
Bold, Guido
Acemoglu, Figan
Tintelnot-Blomley, Marina
Fischer, Jean
De Cian, Andre
A short (7 steps) and efficient (45% overall yield) synthesis of (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-γ-lactone, a versatile intermediate toward possible HIV-1 protease inhibitors, is described. Two examples of trans-α- benzylation of the lactonic ring followed by a regioselective opening of the epoxide (with thiopropanamide) as well as an opening of the lactone ring with L-valine (2-methoxy-ethyl)-amide are also given.
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Doi:10.1039/cc9960001835
(1996)Doi:10.1016/0040-4020(96)00561-3
(1996)Doi:10.1021/acs.orglett.1c00288
(2021)Doi:10.1016/0957-4166(94)80119-3
(1994)Doi:10.1248/cpb.44.1484
(1996)Doi:10.1016/S0960-894X(00)00457-1
(2000)
