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Synlett 2016; 27(19): 2721-2725
DOI: 10.1055/s-0036-1588310
DOI: 10.1055/s-0036-1588310
letter
Diversity-Oriented Synthesis of cis-3,4-Dihydroxylated Piperidine and Its Higher Saturated and Unsaturated Homologues from d-Ribose and Their Glycosidase-Inhibition Study[1]
Further Information
Publication History
Received: 16 June 2016
Accepted after revision: 11 August 2016
Publication Date:
31 August 2016 (online)


Abstract
The synthesis of six-, seven-, and eight-membered cis-dihydroxy azacycles has been accomplished from d-ribose using Vasella reductive amination as a key step and utilization of hydroboration–oxidation, Mitsunobu reaction, and ring-closing metathesis (RCM) reactions in a facile manner. These homologous dihydroxylated heterocyclic scaffolds were subjected to the glycosidase inhibition assays. However, only a moderate inhibitory activity for three out of five compounds was observed against α-glucosidases with a high degree of selectivity.
Key words
cis-dihydroxy azacycles - Vasella reductive amination - hydroboration–oxidation - Mitsunobu reaction - ring-closing metathesis - glycosidase inhibition.Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588310.
- Supporting Information