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Directed synthesis of all four pure stereoisomers of the N,C-Coupled naphthylisoquinoline alkaloid ancistrocladinium A

Seupel, Raina and Hertlein-Amslinger, Barbara and Gulder, Tanja and Stawski, Philipp and Kaiser, Marcel and Brun, Reto and Bringmann, Gerhard. (2016) Directed synthesis of all four pure stereoisomers of the N,C-Coupled naphthylisoquinoline alkaloid ancistrocladinium A. Organic letters, 18 (24). pp. 6508-6511.

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Official URL: http://edoc.unibas.ch/54246/

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Abstract

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.
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology (MPI) > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Kaiser, Marcel and Brun, Reto
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:1523-7060
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:20 Apr 2017 12:50
Deposited On:20 Apr 2017 12:50

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