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Synthesis of macrolide antibiotics. 15. Stereodirected synthesis of erythronolide B according to the coupling scheme of the (C9-C13) + (C7-C8) + (C1-C6) fragments

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

A stereodirected synthesis of erythronolide B from levoglucosane by coupling the C9-C13) + (C7-C8) + (C1-C6) fragments was carried out.

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Literature cited

  1. A. F. Sviridov, M. S. Ermolenko, D. V. Yashunskii, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 438 (1989).

    Google Scholar 

  2. R. B. Woodward, E. Logusch, K. P. Nambiar, et al., J. Am. Chem. Soc.,103, 3213 (1981).

    Google Scholar 

  3. G. Stork and S. D. Rychnowsky, J. Am. Chem. Soc.,109, 1565 (1987).

    Google Scholar 

  4. G. Zweifel and H. Arzoumanian, J. Am. Chem. Soc.,89, 291 (1967).

    Google Scholar 

  5. E. J. Corey and D. J. Brunelle, Tetrahedron Lett., 3409 (1976).

  6. E. Santaniello, F. Ponti, and A. Manzocchi, Synthesis, 891 (1978).

  7. E. J. Corey and L. S. Melvin, Tetrahedron Lett., 929 (1975).

  8. M. Kinoshita, M. Arai, N. Ahsawa, and M. Nakata, Tetrahedron Lett.,27, 1815 (1986).

    Google Scholar 

  9. A. F. Sviridov, M. S. Ermolenko, D. V. Yashunskii, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 151 (1989).

    Google Scholar 

  10. P. F. Wiley, M. V. Sigal, O. Wearer, R. Monahan, and K. Gerzon, J. Am. Chem. Soc.,79, 6070 (1957).

    Google Scholar 

  11. P. L. Tardrew and M. A. Nyman, US Patent 3,127,315 (1964).

  12. J. Martin, T. J. Perun, and R. L. Girolami, Biochemistry,5, 2852 (1966).

    Google Scholar 

  13. R. S. Egan, T. J. Perun, J. R. Martin, and L. A. Mitscher, Tetrahedron,29, 2525 (1973).

    Google Scholar 

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For previous communication, see [1],

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 447–451, February, 1989.

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Sviridov, A.F., Ermolenko, M.S., Yashunskii, D.V. et al. Synthesis of macrolide antibiotics. 15. Stereodirected synthesis of erythronolide B according to the coupling scheme of the (C9-C13) + (C7-C8) + (C1-C6) fragments. Russ Chem Bull 38, 391–395 (1989). https://doi.org/10.1007/BF00953635

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  • DOI: https://doi.org/10.1007/BF00953635

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