Skip to main content
Log in

Synthesis of macrolide antibiotics. Communication 6. Synthesis of C13-EPI-C9-C13 fragment of erythronolide a

  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A rearrangement was discovered of 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-4-O-mesyl-β-D-glactopyranose into 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-5-O-mesyl-α-L-idofuranose.

  2. 2.

    The C13-epi-C9-C13 fragment of erythronolide A was synthesized from levoglucosan in 18 stages in an overall yield of 3.4%.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. A. F. Sviridov, G. E. Berdimbetova, and N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim., 2576 (1982).

  2. A. F. Sviridov, M. S. Ermolenko, and N. K. Kochetkov, Izv. Akad. Nauk SSSR Ser. Khim., 2561 (1982).

  3. G. Wagner and K. Wüthrich, J. Magn. Reson.,33, 675 (1979).

    Google Scholar 

  4. P. Köll, H.-G. John, and J. Schulz, Liebigs Ann. Chem., 613 (1982).

  5. M. Christe, H. J. Reich, and J. D. Roberts, J. Am. Chem. Soc.,93, 3463 (1971).

    Google Scholar 

  6. H.-J. Schneider and V. Hoppen, J. Org. Chem. Soc.,43, 3866 (1978).

    Google Scholar 

  7. K. Omura and D. Swern, Tetrahedron,34, 1651 (1978).

    Google Scholar 

  8. N. Cyr and A. S. Perlin, Can. J. Chem.,57, 2504 (1979).

    Google Scholar 

  9. E. C. Ashby and J. J. Lin, Tetrahedron Lett., 4481 (1977).

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1157–1161, May, 1985.

For Communication 5, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sviridov, A.F., Ermolenko, M.S., Yashunskii, D.V. et al. Synthesis of macrolide antibiotics. Communication 6. Synthesis of C13-EPI-C9-C13 fragment of erythronolide a. Russ Chem Bull 34, 1056–1060 (1985). https://doi.org/10.1007/BF01142801

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01142801

Keywords

Navigation