Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthetic Studies on Carbapenam Skeletons

  • Published : 1996.10.20
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Abstract

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-azabicyclo[3.3.0]octanedicarboxylates (22a-22d, 26a-26d). 2-Oxa-1-azabicyclo[3.3.0]octane-4,8-dicarboxylates (22c-22d, 26c-26d) were transformed to 6-(l-hydroxyethyl)carbapenam-3-carboxylates (30a-30b, 31a-31b).

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References

  1. J. Antibiotics v.32 Kahan, J. S.;Kahan, F. M.;Goegelman, R.;Currie, S. A.;Jackson, M.;Stapley, E. O.;Miller, T. W.;Miller, A. K.;Hendlin, D.;Mochales, S.;Hernandez, S.;Woodruff, H. B.;Birnbaum, J.
  2. J. Am. Chem. Soc. v.100 Albers-Schonberg, G.;Arison, B. H.;Hensens, O. D.;Hirshfield, J.;Hoogsteen, K.;Kaczka, E. A.;Rhones, R. E.;Kahan, J. S.;Kahan, F. M.;Ratcliffe, R. W.;Walton, E.;Ruswinkle, L. J.;Morin, R. B.;Christensen, B. G.
  3. The Chemistry of Thienamycin and Other Carbapenem Antibiotics, Chemistry and Biology of β-Lactam Antibiotics v.2 Ratcliffe, R. W.;Albers-Schonberg, G.;Morin, R. B.;Gorman, M.(Ed.)
  4. Tetrahedron Lett. v.20 Tufariello, J. J.;Lee, G. E.;Senaratine, P. A.;Al-Nuri, M.
  5. J. Org. Chem. v.47 Kametani, T.;Huang, S.-P.;Nakayama, A.;Honda, T.
  6. J. Org. Chem. v.43 Mancuso, A. J.;Huang, S. L.;Swern, D.
  7. J. Am. Chem. Soc. v.62 Stiller, E. T.;Harris, S. A.;Finkelstein, J.;Keresztes, J. C.;Folkers, K.
  8. J. Korean Chem. Soc. v.37 Seo, M. H.;Wang, H. C.;Lee, Y. Y.;Goo, Y. M.
  9. Bull. Korean Chem. Soc. v.14 Seo, M. H.;Wang, H. C.;Lee, Y. Y.;Goo, Y. M.;Kim, K
  10. Synthesis Botteghi, C.;Soccolini, F.