Studies on macrocyclic lactone antibiotics. VIII. Absolute structures of rhizoxin and a related compound.
The absolute structure of rhizoxin, a potent antifungal and antitumor antibiotic, was determined by interrelation with compound 2 whose structure was established by X-ray analysis. Since a 18OH group was introduced at C-3 on a hydrolytic cleavage of C-2, C-3 epoxy group with alkaline H2(18)O, the original epoxy oxygen should be retained at C-2. The stereo-chemistry at C-2 and C-3 positions in rhizoxin was, therefore, determined as 2R,3S.
D055598:Chemical Phenomena; D002621:Chemistry; D007783:Lactones / Q000302:isolation & purification; D018942:Macrolides; D013237:Stereoisomerism
D007783:Lactones; D018942:Macrolides; C041443:rhizoxin