Synthesis and pharmacology of 2,9alpha-dimethyl-2'-hydroxy-6,7-benzomorphan.
2,9alpha-Dimethyl-2'-hydroxy-6,7-benzomorphan (14) has been synthesized in six to seven steps from trans-3,4-dihydro-4-(2-dimethylaminoethyl)-6-methoxy-3-methyl-1(2H)-naphthalenone (1). The key reaction of the sequence was mercuric acetate cyclization of trans-1,2-dihydro-1-(2-methylaminoethyl)-7-methoxy-2-methylnaphthalene (8) which gave a mixture of 9alpha-methyl-8alpha-hydroxy-6,7-benzomorphan (9, 49%), the corresponding acetate (10, 13%), and the 9beta-methyl-8alpha-hydroxy-6,7-benzomorphan (11, 5%). In the presence of Et3N, the yields were 16, 37, and 0%, respectively. Structural assignments are based on ir, NMR, and mass spectral data and on chemical conversions.
D000700:Analgesics / Q000138:chemical synthesis; D000818:Animals; D001575:Benzomorphans / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000882:Haplorhini; D006801:Humans; D008297:Male; D051379:Mice; D008968:Molecular Conformation; D009019:Morphinans / Q000138:chemical synthesis*; D009021:Morphine Dependence / Q000503:physiopathology; D011930:Reaction Time / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013375:Substance Withdrawal Syndrome
D000700:Analgesics; D001575:Benzomorphans; D009019:Morphinans