Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A Stereoselective Synthesis of 1 $\beta$-Aminocarbapenems.

  • Published : 20010600
Download PDF
⟨ Previous Next ⟩

Abstract

A stereoselective synthesis of $1\beta-aminocarbapenems$ (11a-c) starting from-4-acetoxy-2-axetidinone derivative 4 is described. 4-Acetoxy-2-azetidinone derivative (4) was reacted with lithium enolate of benzophenone limine of glycine phenyl ester (5f) to give alkylated product (R)-6f in good yield with high diastereoselectivity. The alkylated procudt (R)-6f was transformed to thioesters (7a-c) by transesterification with thiols, Thioesters (7a-c) were converted to their oxalimides (8a-c), followed by the phosphite-mediated reductive cyclization to give carbapenems (9a-c). Removal of all protecting groups of carbapenems (9a-c) afforded $1\beta-aminocarbapenems$ (11a-c).

Keywords

References

  1. J. Am. Chem. Soc. v.100 no.6491 Albers-Schonberg, G.;Arison, B. H.;Hensens, O. D.;Hirshfield, J.;Hoogsteen, K.;Kaczka, E. A.;Rhodes, R. E.;Kahan, J. S.;Ratcliffe, R. A.;Walton, E.;Ruswinkle, L. J.;Morin, R. B.;Christensen, B. G.
  2. J. Antibioties. v.32 no.1 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.;Hernanadez, S.;Woodruff, H. B.;Birnbaum, J.
  3. Heterocycles. v.21 no.29 Shih, D. H.;Baker, F.;Cama, L.;Chistensen, B. G.
  4. US Appl. 603005. v.23 Cama, L. D.;Christensen, B. G.;Shih, D. H.
  5. Eur. Pat. Appl. EP. v.160 no.876 Cama, L. D.;Christensen, B. G.;Shih, D. H.
  6. Bull. Korean Chem. Soc. v.21 no.767 Seo, K. J.;Lim, M. H.;Moon, J. M.;Goo, Y. M.;Lee, Y. Y.
  7. In the Organic Chemistry of β-Lactams. Kant, J.;Walker, D. G.;Georg, G. I.(Ed.)
  8. J. Org. Chem. v.52 no.2563 Fuentes, L. M.;King, S. A.;Purick, R.;Reamer, R. A.;Schmit, S. M.;Cama, L.;Christensen, B. G.
  9. Synthesis. v.924 Shinkai, I.;Liu, T.;Reamer, R.;Sletzinger, M.
  10. Bull. Chem. Soc. Jpn. v.64 no.57 Toogo, H.;Fujii, M.;Yokoyama, M.
  11. Synlett. v.609 Seki, M.;Kondo, K.;Kuroda, T.;Yamanka, T.;Iwasaki, Y.