Morphinans dihydroxy

The Delft synthesis makes use of an acid-catalyzed ring closure - in fact an intramolecular aromatic alkylation - of a l-(3,5-dihydroxy-4-methoxybenzyl) isoquinoline derivative that is prepared starting from (natural) gallic acid. One of the hydroxyl groups is removed via a Pd/ C hydrogenation of the benzyl ether. Other catalytic steps play an important role some steps were improved recently [27]. The crucial step in the Rice synthesis makes use of a l-(2-bromo-5-hydroxy-4-methoxybenzyl)isoquinoline derivative that is also cyclized in an acid-catalyzed ring closure to the morphinan skeleton, followed by catalytic removal of the bromo substituent (Scheme 5.8). 

Chemical Name 17-Allyl-4,5a-epoxy-3,14-dihydroxy-morphinan-6-one... 

Preparation of 17-(cyclopropylmethyl)-6,7-didehydro-3,14-dihydroxy-4,5a-epoxy-5 -nitropyrido[21,31 6,7]morphinan... 

Several 4-hydroxymorphinan-6-ones bearing a 14-OH function have been made from oxymorphone (108).(1O9) Here there is a marked contrast in the qualitative action observed relative to the actions seen in the 3,14-dihydroxy-morphinans. Whereas, in the latter, high antagonist activities with little agonism occurred, 4-methoxy-14-hydroxy-N-methylmorphinan-6-one (109b), for example, was 6x as potent as morphine in the MHP antinociceptive assay. This activity is 4 x that of the corresponding 3-OH analog. 

Allyl-4,5a-3,14-dihydroxymorphinan-6-one hydrochloride Morphinan-6-one, 4,5-epoxy-3-[4-dihydroxy-17-(2-propenyl)-, hydrochloride, (5a)- (-)-N-Allyl-14-hydroxy-nordihydromorphinone hydrochloride Allylnoroxy-morphone Hydrochloride U.S.P.,... 

Chemical Name 17-allyi-4,5a -epoxy-3,14-dihydroxy-morphinan-6-one Common Name N-aliyInoroxymorphone N-alIyl-1,4-hydroxydihydronormorphinone Structurai Formula ... 

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