Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthetic Studies on Carbapenam Skeletons (Ⅱ)

  • Published : 1998.03.20
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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-alkoxycarbonylmethylnitrone (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).

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References

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