Syntheses of carbapenam skeletons were achieved from 1,3-propanediol through 1,3-dipolar cycloaddition. 3-(Tetrahydropyran-2-yloxy)-(10) and 3-(t-butyldimethylsilyloxy) propanal (13) were obtained from 1,3-propanediol. 3-Hydroxypropanals (10, 13, 14) were reacted with N-hydroxyglycine esters to give C-(2-hydroxyethyl)-N-alkoxycarbonylmethylnitrones (15a-15d). 1,3-Dipolar cycloaddition of the nitrones with methyl acrylate or ethyl crotonate gave 3-(2-hydroxyethyl)isoxazolidines (16a-16b, 17a-17b, 18, 19a-19b). 3-(2-Hydroxyethyl)isoxazolidines (17a, 17c, 19a, 19b) were converted to 3-(2-iodoethyl)isoxazolidines (21a-21d) or 3-phenylthiocarbonylmethylisoxazolidines (25a-25d) which were cyclized to give 2-oxa-1-azabicyclo3.3.0octanedicarboxylates (22a-22d, 26a-26d). 2-Oxa-1-azabicyclo3.3.0octane-4,8-dicarboxylate s (22c-22d, 26c-26d) were transformed to 6-(l-hydroxyethyl)carbapenam-3-carboxylates (30a-30b, 31a-31b).
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