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Total Synthesis of Polyether Antibiotics

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Recent Progress in the Chemical Synthesis of Antibiotics

Abstract

Stereocontrolled total syntheses of three representative complex polyether antibiotics, okadaic acid (1), antibiotic X-206 (2), and salinomycin (3) are described. The first total synthesis of 1 was achieved via coupling of three segments, C1-C14 (4), C15-C27 (16) and C28-C38 (21), synthesized mainly from glucals, in the order of 4 + (16 + 21)by the sulfone carbanion method. The first convergent asymmetric synthesis of 2 was completed through the synthesis and aldol coupling of the C1-C16 (45) and C17-C37 (59) synthons. Coupling of C10-C17 (88) and C18-C30 (95) fragments followed by aldol condensation with С1-С9 aldehyde (62) gave 3.

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References

  1. Wierenga W (1981) in: ApSimon J (ed) The total synthesis of natural products, Wiley, New York, vol 4, p 263.

    Chapter  Google Scholar 

  2. Kishi Y (1983) in: Westley JW (ed) Polyether antibiotics, Dekker, New York, vol 2, p 1

    Google Scholar 

  3. Boivin TLB (1987) Tetrahedron 43: 3309

    Article  CAS  Google Scholar 

  4. Tachibana K, Scheuer PJ, Tsukitani Y, Kikuchi H, Enger DV, Clardy J, Gopichand Y, Schmitz FJ (1981) J Am Chem Soc 103: 2469

    Article  CAS  Google Scholar 

  5. Isobe M, Ichikawa Y, Goto T (1986) Tetrahedron Lett 27: 963

    Article  CAS  Google Scholar 

  6. Isobe M, Ichikawa T, Bai D, Masaki H, Goto T (1987) Tetrahedron 43: 4767

    Article  CAS  Google Scholar 

  7. Isobe M, Ichikawa Y, Goto T (1985) Tetrahedron Lett 26: 5199

    Article  CAS  Google Scholar 

  8. Isobe M, Ichikawa Y, Bai D, Goto T (1985) ibid 26: 5203

    Google Scholar 

  9. Ichikawa Y, Isobe M, Bai D, Goto T (1987) Tetrahedron 43: 4737

    Article  CAS  Google Scholar 

  10. Hosomi A, Sakurai H (1976) Tetrahedron Lett 1295

    Google Scholar 

  11. Ichikawa Y, Isobe M, Goto T (1984) Tetrahedron Lett 25: 5049

    Article  CAS  Google Scholar 

  12. Ichikawa Y, Isobe M, Goto T (1987) Tetrahedron 43: 4749

    Article  CAS  Google Scholar 

  13. Isobe M, Ichikawa Y, Masaki H, Goto T (1984) Tetrahedron Lett 25: 3607

    Article  CAS  Google Scholar 

  14. Ichikawa Y, Isobe M, Masaki H, Kawai T, Goto T (1987) Tetrahedron 43: 4759

    Article  CAS  Google Scholar 

  15. Berger J, Rachlin AI, Scott WE, Sternbach LH, Goldberg MW (1951) J Am Chem Soc 73: 5295

    Article  Google Scholar 

  16. Blount JF, Westley JW (1975) J Chem Soc Chem Commun 533

    Google Scholar 

  17. Evans DA, Bender SL, Morris J (1988) J Am Chem Soc 110: 2506

    Article  CAS  Google Scholar 

  18. Evans DA, Ennis MD, Mathre DJ (1982) J Am Chem Soc 104: 1737

    Article  CAS  Google Scholar 

  19. Evans DA, Bartroli JA, Shih TL (1981) J Am Chem Soc 103: 2127

    Article  CAS  Google Scholar 

  20. Rossiter BE (1985) in: Morrison JD (ed) Asymmetric synthesis, Academic, Orlando, FL, vol 5, chap 7

    Google Scholar 

  21. Felkin H, Frajerman C, Roussi G (1970) Bull Soc Chim Fr 3704

    Google Scholar 

  22. Fukuyama T, Vranesic B, Negri DP, Kishi Y (1978) Tetrahedron Lett 2741

    Google Scholar 

  23. Martin VS, Woodard SS, Katsuki T, Yamada Y, Ikeda M, Sharpless KB (1981) J Am Chem Soc 103: 6237

    Article  CAS  Google Scholar 

  24. Miyazaki Y, Shibuya M, Sugawara H, Kawaguchi O, Hirose C, Nagatsu J, Esumi S (1974) J Antibiot 27: 814

    CAS  Google Scholar 

  25. Kishi Y, Hatakeyama S, Lewis MD (1982) in: Laidler KJ (ed) Front Chem Plenary Keynote Lect IUPAC 28th Congr, 1981, Pergamon, Oxford, p 287

    Google Scholar 

  26. Horita K, Oikawa Y, Nagato S, Yonemitsu O (1988) Tetrahedron Lett 29: 5143

    Article  CAS  Google Scholar 

  27. Horita K, Oikawa Y, Nagato S, Yonemitsu O (1989) Chem Pharm Bull 37: 1717

    CAS  Google Scholar 

  28. Oikawa Y, Yoshioka T, Yonemitsu O (1982) Tetrahedron Lett 23:885

    Article  CAS  Google Scholar 

  29. Oikawa Y, Tanaka T, Horita K, Yonemitsu O (1984) Tetrahedron Lett 25: 5397

    Article  CAS  Google Scholar 

  30. Horita K, Yoshioka T, Tanaka T, Oikawa Y, Yonemitsu O (1986) Tetrahedron 42: 3021

    Article  CAS  Google Scholar 

  31. Horita K, Oikawa Y, Yonemitsu O (1989) Chem Pharm Bull 37: 1698

    CAS  Google Scholar 

  32. Oikawa Y, Tanaka T, Yonemitsu O (1986) Tetrahedron Lett 27: 3647

    Article  CAS  Google Scholar 

  33. Tanaka T, Oikawa Y, Hamada T, Yonemitsu O (1986) Tetrahedron Lett 27: 3651

    Article  CAS  Google Scholar 

  34. Nakajima N, Hamada T, Tanaka T, Oikawa Y, Yonemitsu O (1986) J Am Chem Soc 108:4645

    Article  CAS  Google Scholar 

  35. Nakajima N, Tanaka T, Hamada T, Oikawa Y, Yonemitsu O (1987) Chem Pharm Bull 35: 2228

    CAS  Google Scholar 

  36. Horita K, Nagato S, Oikawa Y, Yonemitsu O (1987) Tetrahedron Lett 28: 3253

    Article  CAS  Google Scholar 

  37. Oikawa Y, Horita K, Yonemitsu O (1985) Tetrahedron Lett 26:1541

    Article  CAS  Google Scholar 

  38. Horita K, Nagato S, Oikawa Y, Yonemitsu O (1989) Chem Pharm Bull 35: 1705

    Google Scholar 

  39. Seyferth D, Simmons HD, Singh G (1965) J Organomet Chem 3: 3371

    Article  Google Scholar 

  40. Seyferth D, Heeren JK, Singh G, Grem SO, Hughes WB (1966) J Organomet Chem 5: 267

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan

    Osamu Yonemitsu & Kiyoshi Horita

Authors
  1. Osamu Yonemitsu
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  2. Kiyoshi Horita
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Editors and Affiliations

  1. Institut de Chimie des Substances Naturelles du C.N.R.S., Avenue de la Terrasse, F-91198, Gif-sur-Yvette Cedex, France

    G. Lukacs (Directeur de Recherche C.N.R.S.) (Directeur de Recherche C.N.R.S.)

  2. University of Tokyo, 7-3-1 Hongo, Bunkyo-ku Tokyo 113, Japan

    M. Ohno

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© 1990 Springer-Verlag Berlin Heidelberg

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Yonemitsu, O., Horita, K. (1990). Total Synthesis of Polyether Antibiotics. In: Lukacs, G., Ohno, M. (eds) Recent Progress in the Chemical Synthesis of Antibiotics. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-75617-7_13

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  • DOI: https://doi.org/10.1007/978-3-642-75617-7_13

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-75619-1

  • Online ISBN: 978-3-642-75617-7

  • eBook Packages: Springer Book Archive

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