Stereochemistry of Radical Cyclizations to Side-Chain Olefinic Bonds - an Approach to Control of the C-9 Center of Morphine
| dc.contributor.author | Parker, K. A. | en |
| dc.contributor.author | Fokas, D. | en |
| dc.date.accessioned | 2015-11-24T17:38:32Z | |
| dc.date.available | 2015-11-24T17:38:32Z | |
| dc.identifier.issn | 0022-3263 | - |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/14508 | |
| dc.rights | Default Licence | - |
| dc.subject | modified curtius reaction | en |
| dc.subject | convenient reagent | en |
| dc.subject | organic-synthesis | en |
| dc.subject | reducing agent | en |
| dc.subject | tris(trimethylsilyl)silane | en |
| dc.subject | (-)-morphine | en |
| dc.subject | reduction | en |
| dc.subject | alkenes | en |
| dc.subject | ketones | en |
| dc.subject | esters | en |
| dc.title | Stereochemistry of Radical Cyclizations to Side-Chain Olefinic Bonds - an Approach to Control of the C-9 Center of Morphine | en |
| heal.abstract | Styrenes of general structure 5 undergo tandem radical cyclization to cis,cis-hydrophenanthrofurans 9, products which contain the carbocyclic skeleton of the morphine alkaloids. Vinylurethane 5E-NHCO(2)Et cyclizes to 9 alpha via the intermediate radical 7E-NHCO(2)Et in the chair-chair conformation. Cyclization of 5Z-NHCO(2)Et also gives predominantly 9 alpha instead of the expected 9 beta. This anomaly is attributed to the isomerization of 5Z to 5E at a rate competitive with that of cyclization. | en |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | Doi 10.1021/Jo00093a026 | - |
| heal.identifier.secondary | <Go to ISI>://A1994NX38400026 | - |
| heal.journalName | Journal of Organic Chemistry | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 1994 | - |
| 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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