Phenol Oxidation and Biosynthesis. Part XII.l Stereochemical Studies Related to the Biosynthesis of the Morphine Alkaloids
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
View Archive Info| Field | Value | |
| Creator |
Barton, D H R
Bhakuni, D S James, R Kirby, G W |
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| Date |
2010-04-29T04:36:24Z
2010-04-29T04:36:24Z 1967 |
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| Identifier |
Journal of Chemical Society (C),1967, 128
http://hdl.handle.net/123456789/538 |
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| 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.
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| Format |
3873060 bytes
application/pdf |
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| Language |
en
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| Subject |
Ozonolysis
Stereochemical Biosynthesis Morphine Alkaloids Phenol Oxidation |
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| Title |
Phenol Oxidation and Biosynthesis. Part XII.l Stereochemical Studies Related to the Biosynthesis of the Morphine Alkaloids
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| Type |
Article
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