Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Eudistomins(I). Preparation of ($\pm$)-N(10)-Benzyloxycarbonyldebromoedudistomin L.

  • Yoon Byung Hee (Department of Chemistry, Yonsei University) ;
  • Lyu Hak Soo (Department of Chemistry, Yonsei University) ;
  • Hahn Jee Hyun (Lab of Organic Chemistry, OCI Research Center) ;
  • Ahn Chan Mug (Department of Chemistry, Yonsei University Wonju College of Medicine)
  • Published : 1992.06.20
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Abstract

Four plausible precursors (21, 22, 24, and 25), just prior to formation of the oxathiazepine ring in eudistomin, were synthesized by the Pictet-Spengler condensation of N-hydroxytryptamine (15) or N-hydroxytryptophan ester (19) with cysteinal derivatives (5 and 10). In the case of the parent compound (21), one of these four precursors, treatment with dihalomethane in the presence of a phase transfer catalyst gave an eudistomin analogue (26) having the oxathiazepine ring in 35-50% yield.

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References

  1. Pure Appl. Chem. v.53 K. L. Rinehart, Jr.;P. D. Shaw;L. S. Shield;J. B. Gloer;G. C. Harbour;M. E. S. Koker;D. Samain;R. E. Schwartz;A. A. Tymiak;D. L. Weller;G. T. Carter;M. H. G. Munro;R. G. Hughes, Jr.;H. E. Renis;E. B. Swynenberg;D. A. Stringfellow;J. J. Vavra;J. H. Coats;G. E. Zurenko;S. L. Kuentzel;L. H. Li;G. J. Bakus;R. C. Brusca;L. L. Craft;D. N. Young;J. L. Conner
  2. J. Am. Chem. Soc. v.106 K. L. Rinehart, Jr.;J. Kobayashi;G. C. Harbour;R. G. Hughes, Jr.;S. A. Mizsak;T. A. Scahill
  3. Tetrahedron Lett. v.28 J. W. Blunt;R. J. Lake;M. H. G. Munro
  4. Heterocycles v.23 S. Y. Han;M. V. Lakshmikantham;M. P. Cava
  5. Tetrahedron Lett. v.27 M. Nakagawa;J. J. Liu;K. Ogata;T. Hino
  6. J. Org. Chem. v.52 R. Plate;R. H. M. Van Hout;H. C. J. Ottenheijm
  7. J. Chem. Soc. Chem. Commun. M. Nakagawa;J. J. Liu;K. Ogata;T. Hino
  8. J. Am. Chem. Soc. v.111 M. Nakagawa;J. J. Liu;T. Hino
  9. Tetrahedron Lett. v.30 I. W. J. Still;J. R. Strautmanis
  10. Tetrahedron Lett. v.30 P. H. H. Hermkens;J. H. V. Maarseveen;C. G. Kruse;H. W. Scheeren
  11. J. Org. Chem. v.55 P. H. H. Hermkens;J. H. V. Maarseveen;H. W. Berens;J. M. M. Smits;C. G. Kruse;H. W. Scheeren
  12. Bull. Korean Chem. Soc. v.12 B. H. Yoon;H. S. Lyu;J. H. Hahn;C. M. Ahn
  13. J. Org. Chem. v.50 D. R. Hwang;P. Helquist;M. S. Shekhani
  14. Bull. Chem. Soc. Jpn. v.43 K. Oki;K. Suzuki;S. Tuchida;T. Saito;H. Katake
  15. Tetrahedron Lett. v.19 C. H. Wong;K. T. Wang
  16. Organic Syntheses v.Ⅳ Th. J. de Boer;H. J. Backer
  17. Chem. Pharm. Bull. v.23 A. Ito;R. Takahashi;Y. Bara
  18. Tetrahedron Lett. v.14 L. I. Zarharkin;I. M. Khorlina
  19. Bull. Chem. Soc. Jpn. v.37 S. Akabori;S. Sakakibara;Y. Shimonishi;Y. Nobuhara
  20. J. Chem. Soc. G. F. Smith
  21. J. Pharm. Sci. v.58 B. T. Ho;W. M. Mclsaac;L. W. Tansey
  22. J. Chem. Soc. E. H. P. Young
  23. Synth. Commun. v.15 R. S. Varma;G. W. Kabalka
  24. J. Am. Chem. Soc. v.100 E. J. Corey;H. Estreicher
  25. Organic Synthesis v.1 K. Oliver
  26. J. Org. Chem. v.47 H. C. J. Ottenheijm;R. Plate;J. H. Noordick;J. D. M. Herscheid
  27. J. Chem. Soc. Chem. Commun. T. L. Gilchrist;D. A. Lingham;T. G. Roberts
  28. J. Chem. Soc., Perkin Trans. 1. T. L. Gilchrist;T. G. Roberts
  29. Chem. Listy. v.51 J. Ratusky;F. Sorm
  30. J. Org. Chem. v.51 R. Plate;P. H. H. Hermkens;J. M. M. Smits;H. C. J. Ottenheijm
  31. Chem. Letters Y. Kigukawa;M. Kawase
  32. Synthesis C. Salvator;M. Antonio;S. Mario
  33. Acta Chem. Scand. v.13 D. Theodoroponlos
  34. Il Farmaco (Pavia) Ed. Sci. v.13 G. Cavallini;V. Ravenna
  35. Chem. Abstr. v.52