Conclusions
-
1.
A new method for the synthesis of macrocyclic ketolactones containing a thiophene ring has been developed.
-
2.
The reductive desulfuration of macrocyclic ketolactones containing a thiophene ring has given ketoalkanolides, in particular that with a 14-membered ring the structure of which is close to that of the cyclic fragment of the natural macrolide antibiotics.
Similar content being viewed by others
Literature cited
Ya. L. Gol'dfarb, S. Z. Taits, and L. I. Belen'kii, Tetrahedron,19, 1851 (1963).
Ya. L. Gol'dfarb, S. Z. Taits, and F. D. Alashev, USSR Authors' Certificate No. 185894 (1965); Izobreteniya. Promyshlennye obraztsy. Tovarnye znaki. Byulleten' No. 18 (1966).
H. Hunsdiecker, H. Erlbach, and E. Fogt, French Patent No. 839, 188 (1938); Chem. Zentr.,1939, II, 2481; H. Hunsdiecker and H. Erlbach, Chem. Ber.,80, 129 (1947).
G. I. Nikishin and G. V. Somov, Dokl. Akad. Nauk SSSR,144, 579 (1962); G. V. Somov, Thesis [in Russian], Moscow (1962), p. 151.
E. W. Spangel and W. H. Carothers, J. Am. Chem. Soc.,58, 654 (1936).
R. B. Woodward, Angew. Chem.,69, 50 (1957).
J. Borowitz and G. J. Williams, Tetrahedron Letters,1965, 3813.
J. Falbe and F. Korte, Chem. Ber.,96, 919 (1963).
Ya. L. Gol'dfarb, S. Z. Taits, T. S. Chirkova, and L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim.,1964, 2055.
S. Z. Taits, L. I. Belen'kii, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim.,1963, 1460; Dokl. Akad. Nauk SSSR,139, 1365 (1961).
Ya. L. Gol'dfarb, S. Z. Taits, and F. D. Alashev, USSR Authors' Certificate No. 184270 (1965); Izobreteniya. Promyshlennye obraztsy. Tovarnye znaki. Byulleten' No. 15 (1966).
Ya. L. Gol'dfarb, S. Z. Taits, and L. I. Belen'kii, Zh. Obshch. Khim.,29, 3654 (1959).
P. R. Jones, R. J. Panicchi, R. M. Stimson, and L. Port, J. Org. Chem.,31, 4277 (1966).
D. Taub, N. N. Girotra, R. D. Hoffsommer, C. H. Kuo, H. L. Slates, S. Weber, and N. L. Wendler, Chem. Comm.,1967, 225.
E. H. Flinn, M. V. Sigal, P. F. Wiley, and K. Gerzon, J. Am. Chem. Soc.,76, 3121 (1954).
V. Plesek, Chem. Listy,50, 561 (1956).
G. Stadnikoff and I. Goldfarb, Ber.,61, 2341 (1928).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 566–572, March, 1968.
Rights and permissions
About this article
Cite this article
Taits, S.Z., Alashev, F.D. & Gol'dfarb, Y.L. A new method for the synthesis of macrocyclic compounds. Russ Chem Bull 17, 550–554 (1968). https://doi.org/10.1007/BF00911609
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00911609