Journal of Organic Chemistry p. 4928 - 4933 (1982)
Update date:2022-08-03
Topics:
Miller, Marvin J.
Bajwa, Joginder S.
Mattingly, Phillip G.
Peterson, Kathleen
Enantioselective syntheses of 3-substituted 4-(alkoxycarbonyl)-2-azetidinones from malic acid have been developed.Alkylation of diesters of D-malic acid provided primarily the erythro products 15RS.Base-mediated inversion gave racemic threo isomers 15.Saponification of 15 and selective monoesterification provided the correspondingly substituted β-hydroxy acids 17, which could also be epimerized at the hydroxyl position.Separate conversion of the isomers 17 to the hydroxamates 18 followed by cyclization gave the desired β-lactams 19 with complete control of stereochemistry.
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Doi:10.1016/S0022-1139(00)82293-9
(1982)Doi:10.1007/BF00809019
(1982)Doi:10.3390/md15110344
(2017)Doi:10.1021/ja00389a048
(1982)Doi:10.1023/B:COHC.0000033548.10379.02
(2004)Doi:10.1248/cpb.39.3180
(1991)
