Vanadium Oxytrichloride Oxidation of Reticuline to Isoboldine1
- 1 January 1973
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 3 (1) , 33-35
- https://doi.org/10.1080/00397917308061999
Abstract
The synthesis of aporphine alkaloids by oxidative coupling of phenolic benzyltetrahydroisoquinolines has been of little utility, primarily because of low yields encountered in the coupling step. The conversion of reticuline (1) to isoboldine (2) is representative in that despite many attempts,2 the maximum yield obtained has been 6%.Keywords
This publication has 6 references indexed in Scilit:
- Model Reactions for the Biosynthesis of Erythrina AlkaloidsAngewandte Chemie International Edition in English, 1971
- Studies on the syntheses of heterocyclic compounds. Part CCCLXXXII. Phenolic oxidative coupling of reticuline by use of various reagentsJournal of the Chemical Society C: Organic, 1971
- Intramolecular oxidative phenol coupling. A new methodJournal of the American Chemical Society, 1969
- ortho-Dienone synthesis by the phenolic oxidation of dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinolineJournal of the Chemical Society C: Organic, 1969
- An improved synthesis of various racemic polyphenolic tetrahydroisoquinoline alkaloidsJournal of Heterocyclic Chemistry, 1968
- Synthesis of a Morphinan Derivative by Oxidative Ring ClosureAngewandte Chemie International Edition in English, 1967