Formic acid catalysed rearrangement of 5beta-methyldihydrothevinols (= 3,6-dimethoxy-5,17-dimethyl-4,5-epoxy-6,14-ethanomorphinan-7-methanols): synthesis of new doubly bridged morphinan derivatives.
We recently showed that substitution of a 5beta-methyl group allows the isolation of 14-alkenyldihydrocodeinones from the action of hot formic acid on certain dihydrothevinols. It has now been shown that, in those dihydrothevinols which are converted to stable side chain olefins by such treatment, introduction of a 5beta-methyl group results in the formation of new doubly bridged morphinan derivatives in addition to the dihydrocodeinones or olefins. The new morphinans have low affinities for opioid receptors.
Rennison
David
D
Department of Pharmacy and Pharmacology, University of Bath, Bath, BA2 7AY, UK.
Grundt
Peter
P
Goodyer
Claire
C
Lewis
John W
JW
Husbands
Stephen M
SM
D000701:Analgesics, Opioid / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D016466:CHO Cells; D002384:Catalysis; D006224:Cricetinae; D005561:Formates / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D009019:Morphinans / Q000138:chemical synthesis* / Q000494:pharmacology; D011485:Protein Binding; D011957:Receptors, Opioid / Q000737:chemistry / Q000378:metabolism
D000701:Analgesics, Opioid; D001952:Bridged-Ring Compounds; D005561:Formates; D009019:Morphinans; D011957:Receptors, Opioid; C030544:formic acid