ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Photooxydation of (+)-3-methoxy-N-methyl-morphinan hydrobromide (I, HBr, Romilar Roche) yields (-)-3-methoxy-10-oxo-N-methyl-morphinan (II). The structure of the compound has been established. The introduction of a carbonyl group in position 10 is easily achieved in good yield also by oxydation with chromic acid. Whereas reduction of the 10-oxo-compound with lithium aluminium hydride leaves the tetracyclic ring structure of the morphinan compound unchanged, reduction according to Clemmensen causes scission of the ring, leading to a tricyclic octahydro-phenanthrene with angular basic side chain, the structure of which has been established by synthesis. Pharmacological tests revealed that the introduction of a carbonyl or hydroxy group in position 10 of the dextro series of morphinans causes a marked decrease in the antitussive activity. The corresponding derivatives of the Zaevo series have almost entirely lost their analgesic activity.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19560390718
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