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Synthesis 2014; 46(19): 2591-2594
DOI: 10.1055/s-0034-1378381
DOI: 10.1055/s-0034-1378381
paper
Synthesis of (+)-Harmicine
Further Information
Publication History
Received: 25 April 2014
Accepted after revision: 11 June 2014
Publication Date:
11 July 2014 (online)
Abstract
A facile convergent access to the important indole alkaloid (+)-harmicine is described, starting from tryptamine and (R)-acetoxysuccinic anhydride via the corresponding acetoxysuccinimide in very good overall yield. Regioselective reduction of an unsymmetrical imide carbonyl group and acid-catalyzed stereoselective intramolecular cyclization were the key features involved. The directing group to induce asymmetry was finally detached via the corresponding iodide by using tributyltin hydride chemistry.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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