Enantioselective synthesis of (-)-dihydrocodeinone: A short formal synthesis of (-)-morphine
| dc.contributor.author | Parker, K. A. | en |
| dc.contributor.author | Fokas, D. | en |
| dc.date.accessioned | 2015-11-24T17:33:55Z | |
| dc.date.available | 2015-11-24T17:33:55Z | |
| dc.identifier.issn | 0022-3263 | - |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/13911 | |
| dc.rights | Default Licence | - |
| dc.subject | lithium aluminum-hydride | en |
| dc.subject | asymmetric reduction | en |
| dc.subject | radical cyclizations | en |
| dc.subject | kinetic resolution | en |
| dc.subject | formamidinesulfinic acid | en |
| dc.subject | enantiomeric purity | en |
| dc.subject | morphine alkaloids | en |
| dc.subject | 5-exo cyclizations | en |
| dc.subject | aminyl radicals | en |
| dc.subject | cyclic-ketones | en |
| dc.title | Enantioselective synthesis of (-)-dihydrocodeinone: A short formal synthesis of (-)-morphine | en |
| heal.abstract | The radical cyclization approach to the morphine alkaloids has been applied in an asymmetric synthesis of (-)-dihydrocodeinone. A chiral cyclohexenol (R-32), from the CBS reduction of the enone, is the source of chirality. The first key step, tandem closure in which stereochemistry is controlled by geometric constraints, (-)-15b -> (+)-16, was followed by an unprecedented reductive hydroamination, completing the synthesis of (-)-dihydroisocodeine ((-)-17) in 13 steps from commercially available materials. | en |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | Doi 10.1021/Jo0513008 | - |
| heal.identifier.secondary | <Go to ISI>://000234837500001 | - |
| heal.journalName | Journal of Organic Chemistry | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 2006 | - |
| heal.publisher | American Chemical Society | en |
| heal.recordProvider | Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Μηχανικών Επιστήμης Υλικών | el |
| heal.type | journalArticle | - |
| heal.type.el | Άρθρο Περιοδικού | el |
| heal.type.en | Journal article | en |
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