1806. Carbomycin
Description and references
Sixteen-membered-ring macrolide antibiotic complex similar to leucomycin, q.v. and erythromycin, q.v., produced by Streptomyces halstedii. Isoln and antibacterial activity: F. W. Tanner et al., Antibiot. Chemother. 2, 441 (1952). Two components have been isolated: Carbomycin A (major) and carbomycin B. Isoln of A: Friedman et al., US 2960438 (1960 to Pfizer); of B: F. A. Hochstein, K. Murai, J. Am. Chem. Soc. 76, 5080 (1954). Structure of A and B: R. B. Woodward, Angew. Chem. 69, 50 (1957); revised structure: M. Kuehne, B. W. Benson, J. Am. Chem. Soc. 87, 4660 (1965); R. B. Woodward et al., ibid. 4662. Abs config of A and B: W. D. Celmer, ibid. 88, 5028 (1966). Identity of A with deltamycin A4: Y. Shimauchi et al., J. Antibiot. 31, 270 (1978). Synthesis of B: K. Tatsuta et al., J. Am. Chem. Soc. 99, 5826 (1977). Stereospecific total synthesis of B: eidem, Tetrahedron Lett. 1980, 2837. Retrosynthetic studies: K. C. Nicolaou et al., J. Am. Chem. Soc. 103, 1222 (1981). Reviews: D. Vazquez, in Antibiotics Vol. 1, D. Gottlieb, P. D. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 366-377; W. Keller-Schierlein in Fortschr. Chem. Org. Naturst. 30, 314-460 (1973).
