A convenient synthesis of delta(7,8)-morphinan-6-one and its direct oxidation to 14-hydroxy-delta(7,8)-morphinan-6-one.
Synthesis of Delta(7,8)-morphinan-6-one by Grewe cyclization and bromoketalization reaction as crucial steps is described. Introduction of a hydroxyl group at 14-position is demonstrated by direct oxidation with MnO(2) in the presence of silica gel.
Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Venezian 21, 20133 Milan, Italy. daniele.passarella@unim.it
Daniele
D
Passarella
Alessandra
A
Consonni
Alessandra
A
Giardini
Giordano
G
Lesma
Alessandra
A
Silvani
D003500:Cyclization; D006865:Hydrogenation; D004091:Hydromorphone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D006878:Hydroxides / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D017895:Manganese Compounds / Q000737:chemistry; D009019:Morphinans / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D010087:Oxides / Q000737:chemistry; D012822:Silicon Dioxide / Q000737:chemistry; D013237:Stereoisomerism
C470890:(7,8)-morphinan-6-one; C470891:14-hydroxy-(7,8)-morphinan-6-one; D006878:Hydroxides; D007659:Ketones; D017895:Manganese Compounds; D009019:Morphinans; D010087:Oxides; D012822:Silicon Dioxide; C031356:hydroxide ion; D004091:Hydromorphone; C016552:manganese dioxide