279 



Tetracycline, Analogues and Related Substances 



607 



6-Pyrromycinone occurs as such and also as the chro- 

 mophore of the antibiotics pyrromycin and the cinerubins. 

 It is identical with rutilantinone. 



Hans Brockmann and Werner Lenk, Chem. Ber. 92 1880 

 (1959). (Structure) 



Idem., Naturwissenschaften 47 135 (1960). (Revised 

 structure) 



H. Brockmann, H. Brockmann, Jr., J. J. Gordon, W. Keller- 

 Schierlein, W. Lenk, W. D. Ollis, V. Prelog and I. O. Suther- 

 land, Tetrahedron Letters No. 8, p. 25 (1960). 



W. D. Ollis, I. O. Sutherland and J. J. Gordon, Tetrahedron 

 Letters No. 16, p. 17 (1959). 



7-Chloro-5a(Ila)-dehydrotetracycline, C<,.H.iOsN^Cl, [ajo^' 15.5° 

 (c 0.65 in 0.03 N hydrochloric acid). 



CONH2 

 OH O O O 



Streptomyces aiireofaciens Duggar inutant 



The analogous compounds in which the chlorine atom 



is replaced by H and Br are also claimed. 



J. R. D. McCormick, Philip A. Miller, John A. Growich, 



Newell O. Sjolander and Albert P. Doerschuk, /. A?n. Chem. 



Soc. 80 5572 (1958). 



608 Chlortetracycline (Aureomycin, Biomycin), C22H23O8N2CI, fine 

 yellow crystals, m.p. 168°, [aln'' -274.9° (in methanol). 



CH3 CH3 



CONH2 

 OH O OH O 



Streptomyces aureofaciens 



R. W. Broschard, A. C. Dornbush, S. Gordon, B. L. Hutch- 

 ings, A. R. Kohler, G. Krupka, S. Kuchner, D. V. Lefemine and 

 C. Pidacks, Science 109 199 (1949). (Isolation) 



Benjamin M. Duggar, U. S. Patent 2,482,055 (1949). 



C. R. Stephens, L. H. Conover, F. A. Hochstein, P. P. Regna, 

 F. J. Pilgrim, K. J. Brunings and R. B. Woodward, /. Am. 

 Chem. Soc. 74 4976 (1952). 



