Conclusions
-
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.
The C13-epi-C9-C13 fragment of erythronolide A was synthesized from levoglucosan in 18 stages in an overall yield of 3.4%.
Similar content being viewed by others
Literature cited
A. F. Sviridov, G. E. Berdimbetova, and N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim., 2576 (1982).
A. F. Sviridov, M. S. Ermolenko, and N. K. Kochetkov, Izv. Akad. Nauk SSSR Ser. Khim., 2561 (1982).
G. Wagner and K. Wüthrich, J. Magn. Reson.,33, 675 (1979).
P. Köll, H.-G. John, and J. Schulz, Liebigs Ann. Chem., 613 (1982).
M. Christe, H. J. Reich, and J. D. Roberts, J. Am. Chem. Soc.,93, 3463 (1971).
H.-J. Schneider and V. Hoppen, J. Org. Chem. Soc.,43, 3866 (1978).
K. Omura and D. Swern, Tetrahedron,34, 1651 (1978).
N. Cyr and A. S. Perlin, Can. J. Chem.,57, 2504 (1979).
E. C. Ashby and J. J. Lin, Tetrahedron Lett., 4481 (1977).
Author information
Authors and Affiliations
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
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
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01142801