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Synthesis of (−)- and (+)-2-hydroxy-6-keto-N-methylmorphinans, their O-methyl ethers, and 2-deoxy congeners
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| Zeitschriftentitel: | Canadian Journal of Chemistry |
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| Personen und Körperschaften: | , |
| In: | Canadian Journal of Chemistry, 60, 1982, 24, S. 3055-3060 |
| Format: | E-Article |
| Sprache: | Französisch |
| veröffentlicht: |
Canadian Science Publishing
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| Schlagwörter: |
| Zusammenfassung: | <jats:p> Bischler–Napieralski cyclization of the known phenylacetamide 1, followed by selective ether cleavage of the 3,4-dihydroisoquinoline 2 and sodium borohydride reduction, afforded the tetrahydroisoquinoline 4. Optical resolution of 4 with tartaric acid gave the optical isomers 4a,b, which were converted into the 6-ketomorphinans 9a,b and their O-methyl ethers 10a,b by the following reaction sequence: Birch reduction, N-formylation of the dihydro bases, Grewe cyclization, removal of the N-formyl protecting groups, reductive N-methylation, and O-methylation. The 2-deoxy congeners 12a,b were obtained from 9a,b by phenyltetrazolylation, and catalytic removal of the heterocyclic etherfunction. The (−)-enantiomer 12a obtained by this synthesis was identical with material prepared from natural morphine, and exhibited the high antinociceptive potency already reported. </jats:p> |
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| Umfang: | 3055-3060 |
| ISSN: |
1480-3291
0008-4042 |
| DOI: | 10.1139/v82-437 |