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| 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 |
| Citation: | Journal of Chemical Society (C),1967, 128 |
| Abstract: | 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: | http://hdl.handle.net/123456789/538 |
| Appears in Collections: | Medicinal and Process Chemistry
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| J. Chem. Soc.- 1968-128-132.pdf | | 3782Kb | Adobe PDF | View/Open |
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