Tetrahedron Letters p. 857 - 860 (1992)
Update date:2022-08-04
Topics:
Frazier, Jeffery W.
Staszak, Mike A.
Weigel, Leland O.
Sodium erythorbate (7) has been converted to loracarbef (1). Oxidation of sodium erythorbate to D erythronolactone (8) followed by selective monotosylation and treatment with sodium ethoxide provided ethyl (2S,3R) 4 hydroxy 2.3 epoxybutyrate (10). Swern oxidation of this epoxide into the aldehyde (11), imine formation with tert-butylglycinate and an enantioselective Staudinger reaction with phthalimidoacetyl chloride afforded the (3S,4S)-cis-β-lactam (13). Appropriate functional group manipulations followed by a Dieckmann condensation, chlorination, and protecting group removals gave the enantiomerically pure nucleus of loracarbef (24).
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Doi:10.1007/s11164-012-0875-4
(2013)Doi:10.1039/c2cc36470k
(2012)Doi:10.1021/acs.jmedchem.6b00939
(2016)Doi:10.1007/s00044-012-0278-5
(2013)Doi:10.1039/c39920000399
(1992)Doi:10.1016/S0040-4039(00)91652-6
(1992)