Palladium-Catalyzed Ullmann Cross-Coupling/Tandem Reductive Cyclization Route to Key Members of the Uleine Alkaloid Family
Date
2016-04-01
Authors
Tang, Fei
Banwell, Martin
Willis, Anthony
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
Abstract
The trisubstituted cyclohexenone 12, generated through a palladium-catalyzed Ullmann cross-coupling reaction between o-iodonitrobenzene and a 4,5-trans-disubstituted 2-iodo-2-cyclohexen-1-one, engaged in a tandem reductive cyclization process upon exposure to hydrogen gas in the presence of Raney cobalt. As a result, the 1,5-methanoazocino[4,3-b]indole 13 was obtained and this could be readily elaborated to the racemic modifications of the alkaloids uleine, dasycarpidone, noruleine, and nordasycarpidone (1-4, respectively).
Description
Keywords
alkaloids, azocines, bridged-ring compounds, catalysis, cobalt, cyclization, cyclohexanones, indoles, molecular structure, nitrobenzenes, palladium
Citation
Collections
Source
The Journal of organic chemistry
Type
Journal article
Book Title
Entity type
Access Statement
Open Access
License Rights
Restricted until
Downloads
File
Description