Tetracycline 6-deoxy-5-hydroxy

The 7-chloro-derivative, the first of the group to be isolated (1948) is known as chlortetracy-cline. The 5-hydroxy-derivative is oxytetracy-dine. More recently introduced tetracyclines are 6-demethyl-7-chlorotetracycline and 5-hydroxy-6-deoxy-6-methyienetetracycline. 

Fig. 1. Tetracycline (1) and its derivatives chlortetracycline (7-chlorotetracycline) (2) oxytetracycline (5-hydroxytetracycline) (3), demeclocycline (6-demethyl-7-chlorotetracycline) (4) methacycline (6-demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline) (5) doxycycline (6a-deoxy-5-hydroxytetracycline) (6) and minocycline (6-demethy1-6-deoxy-7-dimethy1 amino tetracycline) (7). Substituents at positions not specifically...

Similar transformations have not as yet been successfully applied to the tetracyclines bearing a hydroxy group at Cs, and no mutant culture has been reported that biosynthesizes a 6-deoxy-5-oxytetracycline. However, other means have been found to avoid 5a,6-dehydration in this subfamily. Treatment of 3 with N-... 

---