Total Synthesis of Lincomycin and Related Chemistry

  • Adam Gołebiowski
  • Janusz Jurczak

Abstract

The presented review describes total syntheses directed towards 6-amino-6,8-dideoxy-D-erythro-D- galacto-octose, commonly named lincosamine – the sugar component of the antibiotic lincomycin. In the first part we present total syntheses of lincosamine that start from carbohydrate precursors. The D-galactose-derived aldehyde is the most frequently used synthon. In the second part, total syntheses of lincosamine from non-carbohydrate precursors are presented. This part of the review is divided into two subsections. The first one groups syntheses based on the application of furan compounds. In the second one we present a hetero-Diels-Alder approach to the synthesis of lincosamine.

Keywords

Aldehyde Adduct Epoxide Azide Oxime 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Mason DJ, DeBoer C (1963) Antimicrob Ag Chemother 1962: 554Google Scholar
  2. 2.
    Herr RR, Bergy MA (1963) Antimicrob Ag Chemother 1962: 560Google Scholar
  3. 3.
    Hoeksema H, Bannister B, Birkenmeyer RD, Kagan F, Magerlein BJ, MacKellar FA, Schroeder W, Slomp G, Herr RR (1964) J Am Chem Soc 86: 4223CrossRefGoogle Scholar
  4. 4.
    Herr RR, Slomp G (1967) J Am Chem Soc 89: 2444CrossRefGoogle Scholar
  5. 5.
    Schroeder W, Bannister B, Hoeksema H (1967) J Am Chem Soc 89: 2448CrossRefGoogle Scholar
  6. 6.
    Slomp G, MacKellar FA (1967) J Am Chem Soc 89: 2454CrossRefGoogle Scholar
  7. 7.
    Magerlein BJ, Birkenmeyer RD, Herr RR, Kagan F (1967) J Am Chem Soc 89: 2459CrossRefGoogle Scholar
  8. 8.
    Shipman LL, Christoffersen RE, Cheney BV (1974) J Med Chem 17: 583CrossRefGoogle Scholar
  9. 9.
    Cheney BV (1974) J Med Chem 17: 590CrossRefGoogle Scholar
  10. 10.
    Mizsak S, Slomp G, Neszmelyi A, Gero SD, Lukacs G (1977) Tetrahedron Lett 721Google Scholar
  11. 11.
    Magerlein BJ (1977) In: Pearlman D (ed) Structure activity relationships among the semisynthetic antibiotics, Academic, New York, p 601Google Scholar
  12. 12.
    Bannister B (1984) Tetrahedron 40: 1633CrossRefGoogle Scholar
  13. 13.
    Bannister B (1972) J Chem Soc Perkin Trans I 3025 and 3031CrossRefGoogle Scholar
  14. 14.
    Magerlein BJ (1970) Tetrahedron Lett 33Google Scholar
  15. 15.
    Horton D, Nakadate M, Tronchet JMJ (1968) Carbohyd Res 7: 56CrossRefGoogle Scholar
  16. 16.
    Howarth GB, Szarek WA, Jones JKN (1970) J Chem Soc (C) 2218Google Scholar
  17. 17.
    Lance DG, Szarek WA, Jones JKN, Howarth GB (1969) Can J Chem 47: 2871CrossRefGoogle Scholar
  18. 18.
    Howarth GB, Lance DG, Szarek WA, Jones JKN (1969) Can J Chem 47: 75CrossRefGoogle Scholar
  19. 19.
    Saeki H, Ohki E (1969) Chem Pharm Bull 17: 1974; ibid. (1970) 18: 412; ibid. (1970) 18: 789CrossRefGoogle Scholar
  20. 20.
    Hoeksema H (1965) Abstr. Pap. 149th Meet Am Chem Soc Detroit p9-CGoogle Scholar
  21. 21.
    Hems R, Horton D, Nakadate M (1972) Carbohydr Res 25: 205CrossRefGoogle Scholar
  22. 22.
    Atsumi T, Fukumaru T, Ogawa T, Matsui M (1973) Agr Biol Chem 37: 2621CrossRefGoogle Scholar
  23. 23.
    Atsumi T, Fukumaru T, Matsui M (1973) Agr Biol Chem 37: 2627CrossRefGoogle Scholar
  24. 24.
    Fukumaru T, Atsumi T, Ogawa T, Matsui M (1973) Agr Biol Chem 37: 2617CrossRefGoogle Scholar
  25. 25.
    David SM, Fisher JC (1974) Carbohydr Res 38: 147CrossRefGoogle Scholar
  26. 26.
    Woolard GR, Rathbone EB, Szarek WA, Jones JKN (1976) J Chem Soc Perkin Trans I, 950CrossRefGoogle Scholar
  27. 27.
    Gateau-Olesker A, Sepulchre AM, Vass G, Géro SD (1977) Tetrahedron 33: 393CrossRefGoogle Scholar
  28. 28.
    Hoppe I, Schöllkopf U (1980) Liebigs Ann Chem 1474Google Scholar
  29. 29.
    Wagle DR, Manhas MS, Bose AK (private communication)Google Scholar
  30. 30.
    Achmatowicz Jr. O, Bukowski P, Szechner B, Zwierzchowska Z, Zamojski A (1971) Tetrahedron 27: 1973CrossRefGoogle Scholar
  31. 31.
    Zamojski A, Banaszek A, Grynkiewicz G (1982) Adv Carbohydr Chem Biochem 40: 1CrossRefGoogle Scholar
  32. 32.
    Szechner B (1981) Tetrahedron 37: 949CrossRefGoogle Scholar
  33. 33.
    Jorgensen MJ (1970) Org React. 18: 1Google Scholar
  34. 34.
    Jurczak J, Raczko J, Golebiowski A (unpublished results)Google Scholar
  35. 35.
    Jurczak J, Raczko J, Golebiowski A, Angew Chem (to be published)Google Scholar
  36. 36.
    Jurczak J, Pikul S (1986) Tetrahedron Lett 26: 3039CrossRefGoogle Scholar
  37. 37.
    Pikul S, Jurczak J, Grynkiewicz G (1987) Bull Pol Ac.: Chem 35: 293Google Scholar
  38. 38.
    Jurczak J, Zamojski A (1972) Tetrahedron 28: 1505CrossRefGoogle Scholar
  39. 39.
    Jurczak J, Chmielewski M, Filipek S (1979) Synthesis 41Google Scholar
  40. 40.
    Danishefsky S, Larson E, Askin D, Kato N (1985) J Am Chem Soc 107: 1246CrossRefGoogle Scholar
  41. 41.
    Jurczak J, Golebiowski A (1989) Chem Rev 89: 149CrossRefGoogle Scholar
  42. 42.
    Chmielewski M, Achmatowicz Jr. O, Zamojski A (1984) Bull Pol Ac Chem 32: 19Google Scholar
  43. 43.
    Chmielewski M, Doboszewski B, Achmatowicz Jr. O, Zamojski A (1984) Bull Pol Ac Chem 32: 423Google Scholar
  44. 44.
    Larson ER, Danishefsky S (1983) J Am Chem Soc 105: 6715CrossRefGoogle Scholar
  45. 45.
    Danishefsky S, Larson E, Springer JP (1985) J Am Chem Soc 107: 1274CrossRefGoogle Scholar
  46. 46.
    Luche JL, Gemal AL (1979) J. Am Chem Soc 101: 5848CrossRefGoogle Scholar
  47. 47.
    Jurczak J, Golebiowski A, Bauer T (1985) Synthesis 928Google Scholar
  48. 48.
    Jurczak J, Bauer T (1986) Tetrahedron 42: 5045CrossRefGoogle Scholar
  49. 49.
    Jurczak J, Bauer T, Golebiowski A (1985) Bull Pol Ac Chem 33: 397Google Scholar
  50. 50.
    Jurczak J, Golebiowski A, Raczko J (1988) Tetrahedron Lett 29: 5975CrossRefGoogle Scholar
  51. 51.
    Jurczak J, Golebiowski A, Raczko J, J Org Chem (to be published)Google Scholar
  52. 52.
    Golebiowski A, Jurczak J (to be published)Google Scholar
  53. 53.
    Cram DJ, Abd Elhafez FA (1952) J Am Chem Soc 74: 5827Google Scholar
  54. 54.
    Chérest, M, Felkin H, Prudent N (1966) Tetrahedron Lett 2199Google Scholar
  55. 55.
    Anh NT (1980) Top Curr Chem 88: 145CrossRefGoogle Scholar
  56. 56.
    Jurczak J, Golebiowski A, Bauer T (to be published)Google Scholar
  57. 57.
    Noyori R, Murata S, Suzuki M (1981) Tetrahedron 37: 3899CrossRefGoogle Scholar
  58. 58.
    Danishefsky S, Maring CJ (1985) J Am Chem Soc 107: 1269CrossRefGoogle Scholar
  59. 59.
    Golebiowski A, Jurczak J, Krajewski JW, Galitskii NM, Verenich AJ, Bull Pol Ac. Chem (in press)Google Scholar
  60. 60.
    Sweet F, Brown RK (1966) Can J Chem 1571Google Scholar
  61. 61.
    Golebiowski A (1987) Chiral α-amino aldehydes in the synthesis of natural products. Thesis, Institute of Organic Chemistry, Polish Academy of Sciences, WarsawGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1990

Authors and Affiliations

  • Adam Gołebiowski
    • 1
  • Janusz Jurczak
    • 1
  1. 1.Institute of Organic ChemistryPolish Academy of SciencesWarszawaPoland

Personalised recommendations