Synthesis of deuterated methylenecyclohexanes, methylenedecalins and taraxasterols
| Autor: | Hsiu-Pu Daniel Lee, Larry S. Eichmeier, David M. Piatak |
|---|---|
| Rok vydání: | 1983 |
| Předmět: |
chemistry.chemical_classification
Ketone Double bond Organic Chemistry Ring (chemistry) Biochemistry Medicinal chemistry Analytical Chemistry chemistry.chemical_compound chemistry Bromide Drug Discovery Wittig reaction Organic chemistry Moiety Radiology Nuclear Medicine and imaging Methylene Spectroscopy Methyl group |
| Zdroj: | Journal of Labelled Compounds and Radiopharmaceuticals. 20:1395-1405 |
| ISSN: | 0362-4803 |
| DOI: | 10.1002/jlcr.2580201211 |
| Popis: | Taraxasterols specifically labelled at various ring E sites were synthesized as were cyclohexanes and decalins substituted by a methyl group and an exocyclic methylene moiety similar to the ring Esystem of this terpene. Preparation of deuterated analogs in which the deuterium is located beta to the exocyclic double bond was accomplished by catalytic reduction of the corresponding unsaturated ketone, followed by removal of the label at the alpha carbon and introduction of the exocyclic methylene with a Wittig reaction. Compounds labelled on the exocyclic methylene moiety were afforded by a Wittig reaction of the appropriate ketone with (methyl-d3)triphenylphosphonium bromide. Taraxasterol trideuterated alpha to the double bond was prepared by DC1 exchange of the ketone followed by a Wittig reaction. |
| Databáze: | OpenAIRE |
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