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Synthesis of macrolide antibiotics. 14. Synthesis of 1-methylene-3,5-O-isopropylidene-9,11-O-p-(methoxybenzylidene)-9(S)-dihydro derivative of seco acid of 9(S)-dihydroerythronolide B

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

Conclusions

A directed synthesis of a seco-acid derivative of 9(S)-dihydroerythronolide B has been 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. 1, 165 (1989).

    Google Scholar 

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

    Google Scholar 

  3. R. B. Woodward, E. Logusch, and K. P. Nambiar, J. Am. Chem. Soc.,103, 3213 (1981).

    Google Scholar 

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

    Google Scholar 

  5. A. F. Sviridov, M. S. Ermolenko, D. V. Yashunskii, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 158 (1989).

    Google Scholar 

  6. A. F. Sviridov, D. V. Yashunskii, M. S. Ermolenko, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1166 (1985).

    Google Scholar 

  7. Y. Oikawa, T. Yoshioka, and O. Yonemitsu, Tetrahedron Lett.,23, 889 (1982).

    Google Scholar 

  8. A. F. Sviridov, M. S. Ermolenko, and N. K. Kochetkov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2561 (1982).

    Google Scholar 

  9. A. G. Kelly and J. S. Roberts, J. Chem. Soc. Chem. Commun., 2542 (1961).

  10. T. J. Barton and C. R. Tully, J. Org. Chem.,43, 3649 (1978).

    Google Scholar 

  11. D. Seebach, M. Ertas, R. Locher, and W. B. Schweitzer, Helv. Chim. Acta,68, 264 (1985).

    Google Scholar 

  12. S. Masamune and W. Choy, Aldrichimica Acta,15, 47 (1982).

    Google Scholar 

  13. I. Nakagawa and T. Hata, Tetrahedron Lett., 1409 (1975).

  14. K. K. Andersen, W. Gaffield, N. E. Papani-Kobaou, et al., J. Am. Chem. Soc.,86, 5637 (1964).

    Google Scholar 

  15. D. R. Williams, J. G. Phillips, and F. H. White, Tetrahedron,42, 3003 (1986).

    Google Scholar 

  16. J. Drabowicz and S. Oae, Synthesis, 404 (1977).

  17. H. J. Dauben, L. R. Honnen, and K. M. Harmon, J. Org. Chem.,25, 1442 (1960).

    Google Scholar 

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For previous communication, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 438–447, February, 1989.

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Sviridov, A.F., Ermolenko, M.S., Yashunskii, D.V. et al. Synthesis of macrolide antibiotics. 14. Synthesis of 1-methylene-3,5-O-isopropylidene-9,11-O-p-(methoxybenzylidene)-9(S)-dihydro derivative of seco acid of 9(S)-dihydroerythronolide B. Russ Chem Bull 38, 382–391 (1989). https://doi.org/10.1007/BF00953634

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  • DOI: https://doi.org/10.1007/BF00953634

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