Directed synthesis of all four pure stereoisomers of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A
The first preparation of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A and its likewise naturally occurring minor atropisomer, in an atropisomerically pure form, is described. The synthesis succeeded by resolution of the already rotationally hindered, and thus atropo-diastereomer...
| Hlavní autoři: | , , , , , , |
|---|---|
| Médium: | Journal article |
| Jazyk: | English |
| Vydáno: |
American Chemical Society
2016
|
| _version_ | 1826274032037658624 |
|---|---|
| author | Seupel, R Hertlein-Amslinger, B Gulder, T Stawski, P Kaiser, M Brun, R Bringmann, G |
| author_facet | Seupel, R Hertlein-Amslinger, B Gulder, T Stawski, P Kaiser, M Brun, R Bringmann, G |
| author_sort | Seupel, R |
| collection | OXFORD |
| description | The first preparation of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A and its likewise naturally occurring minor atropisomer, in an atropisomerically pure form, is described. The synthesis succeeded by resolution of the already rotationally hindered, and thus atropo-diastereomeric acetamide precursors, which were then, without major loss of stereochemical information, cyclized to the respective target molecules. The strategy was applied to the first synthesis of the regioisomeric product ancistrocladinium D, likewise in a stereochemically pure form. |
| first_indexed | 2024-03-06T22:37:16Z |
| format | Journal article |
| id | oxford-uuid:5a532ddb-e85f-4bc8-bc59-cb3e79d8eb93 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T22:37:16Z |
| publishDate | 2016 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:5a532ddb-e85f-4bc8-bc59-cb3e79d8eb932022-03-26T17:15:07ZDirected synthesis of all four pure stereoisomers of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium AJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:5a532ddb-e85f-4bc8-bc59-cb3e79d8eb93EnglishSymplectic Elements at OxfordAmerican Chemical Society2016Seupel, RHertlein-Amslinger, BGulder, TStawski, PKaiser, MBrun, RBringmann, GThe first preparation of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A and its likewise naturally occurring minor atropisomer, in an atropisomerically pure form, is described. The synthesis succeeded by resolution of the already rotationally hindered, and thus atropo-diastereomeric acetamide precursors, which were then, without major loss of stereochemical information, cyclized to the respective target molecules. The strategy was applied to the first synthesis of the regioisomeric product ancistrocladinium D, likewise in a stereochemically pure form. |
| spellingShingle | Seupel, R Hertlein-Amslinger, B Gulder, T Stawski, P Kaiser, M Brun, R Bringmann, G Directed synthesis of all four pure stereoisomers of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A |
| title | Directed synthesis of all four pure stereoisomers of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A |
| title_full | Directed synthesis of all four pure stereoisomers of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A |
| title_fullStr | Directed synthesis of all four pure stereoisomers of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A |
| title_full_unstemmed | Directed synthesis of all four pure stereoisomers of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A |
| title_short | Directed synthesis of all four pure stereoisomers of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A |
| title_sort | directed synthesis of all four pure stereoisomers of the n c coupled naphthylisoquinoline alkaloid ancistrocladinium a |
| work_keys_str_mv | AT seupelr directedsynthesisofallfourpurestereoisomersofthenccouplednaphthylisoquinolinealkaloidancistrocladiniuma AT hertleinamslingerb directedsynthesisofallfourpurestereoisomersofthenccouplednaphthylisoquinolinealkaloidancistrocladiniuma AT guldert directedsynthesisofallfourpurestereoisomersofthenccouplednaphthylisoquinolinealkaloidancistrocladiniuma AT stawskip directedsynthesisofallfourpurestereoisomersofthenccouplednaphthylisoquinolinealkaloidancistrocladiniuma AT kaiserm directedsynthesisofallfourpurestereoisomersofthenccouplednaphthylisoquinolinealkaloidancistrocladiniuma AT brunr directedsynthesisofallfourpurestereoisomersofthenccouplednaphthylisoquinolinealkaloidancistrocladiniuma AT bringmanng directedsynthesisofallfourpurestereoisomersofthenccouplednaphthylisoquinolinealkaloidancistrocladiniuma |