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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 19, Number 3
BKCSDE 19(3)
March 20, 1998 

 
Title
Synthetic Studies on Carbapenam Skeletons (II)
Author
Min Hyo Seo, Yang Mo Goo, Youn Young Lee*
Keywords
Abstract
Syntheses of carbapenam skeletons were achieved from 3-benzyloxypropanal through 1,3-dipolar cycloaddition. 3-Benzyloxypropanal was reacted with N-hydroxyglycine ester to give C-(2-benzyloxyethyl)-N-alkoxycarbonylmethylnitron e (6). 1,3-Dipolar cycloaddition of the nitrone with ethyl crotonate gave 3-(2-benzyloxyethyl)isoxazolidine (7). Compound 7 was transformed to 4-(2-hydroxyethyl)-2-azetidinone (11). Compound 11 was converted to 4-(2-iodoethyl)-2-azetidinone (13) or 4-phenylthiocarbonylmethyl-2-azetidinone (16) which was cyclized to give 6-(1-hydroxyethyl)carbapenam-3-carboxylate (14, 17).
Page
335 - 339
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