جهت دسترسی به کاربرگه ی زیر، از این لینک استفاده کنید. http://78.39.227.9/handle/Hannan/18352
Title: Phenol Oxidation and Biosynthesis. Part XII.l Stereochemical Studies Related to the Biosynthesis of the Morphine Alkaloids
Authors: Barton, D H R;Bhakuni, D S;James, R;Kirby, G W
Keywords: Ozonolysis;Stereochemical;Biosynthesis;Morphine Alkaloids;Phenol Oxidation
Issue Date: 1967
Description: Ozonolysisof tritiated salutaridinols-I and -II has afforded glycericacids whose absolute configurations have been determined bythe isotope dilution method. In this way the stereochemistry of salutaridinol-I, the precursor of the morphine alkaloids, has been defined unambiguously. Oxidation of tritiated (+) - and (-) -reticuline,followed by isotope dilution analysis, has confirmed the configurational relationship between benzylisoquinoline and morphine alkaloids. The results obtained amount to a long sought total synthesis of morphine from reticuline following the biogenetic route. The configurational relationship between morphine and benzylisoquinoline alkaloids has been further confirmed by the reduction of salutaridine to give, after appropriate methylation, (-)-Iaudanosine. The bond broken in this reduction is the bond formed in the biogenetic oxid;3tivecyclisation of (-) -reticuline.
URI: Journal of Chemical Society (C),1967, 128
http://hdl.handle.net/123456789/538
Appears in Collections:Medicinal and Process Chemistry

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