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Synthesis 2016; 48(13): 2065-2068
DOI: 10.1055/s-0035-1561608
DOI: 10.1055/s-0035-1561608
paper
Improved Synthesis of MDL 73811 – A Potent AdoMetDC Inhibitor and Anti-Trypanosomal Compound
Further Information
Publication History
Received: 11 February 2016
Accepted after revision: 09 March 2016
Publication Date:
13 April 2016 (online)
Abstract
An improved synthesis of MDL 73811 – a potent AdoMetDC (S-adenosylmethionine decarboxylase) inhibitor and anti-trypanosomal compound with in vivo activity – has been completed in four steps from commercially available 2′,3′-O-isopropylideneadenosine. Utilization of Mitsunobu chemistry was crucial for the reliable and scalable introduction of the 5′-methylamine moiety, which was problematic using traditional activation/displacement chemistry as previously reported. All reactions in this synthesis were run on gram-scale resulting in a five-fold increase in yield over the original synthesis.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561608.
- Supporting Information
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