Syntheses of corliolin, 1-deoxy-1-ketocoriolin and 1,8-dideoxy-1,8-diketocoriolin from coriolin B.
Hydrolysis of 5,8-di-O-tetrahydropyranyl-5-deoxo-5-hydroxycoriolin which was prepared from coriolin B, followed by oxidation of the hydroxy groups at C-5, or C-1 and C-5, or C-1, C-5 and C-8 afforded coriolin (2), 1-deoxy-1-ketocoriolin (3) and 1,8-dideoxy-1,8-diketocoriolin (4). All three ketones were found to have antitumor activity, whereas antibacterial activity was observed in 2 and 3 but not in 4.
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D001419:Bacteria / Q000187:drug effects; D004352:Drug Resistance, Microbial; D051379:Mice; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000494:pharmacology
D000903:Antibiotics, Antineoplastic; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C007127:coriolin; C026687:1-deoxy-1-ketocoriolin; C026688:1,8-dideoxy-1,8-diketocoriolin