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Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships |
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| Authors: | Alison A Edwards Gangadharar J Sanjayan Raquel Soengas George E Tranter |
| Institution: | a Biological Chemistry, Division of Biomedical Sciences, Imperial College, London SW7 2AZ, UK b Division of Organic Synthesis, National Chemical Laboratory, Pune 411 008, India c Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK d Departamento de Quimica Fundamental, Facultad de Ciencias, Campus da Zapateira, Universidad de A Coruña, 15071 A Coruña, Spain |
| Abstract: | Templated tetrahydrofuran-based γ-azido esters were prepared with the C-2 and C-4 functionalities in cis and trans relative configurations. This was achieved by ring contraction of the suitably protected 2-O-triflates of pentono-1,5-lactones (d-ribose and l-arabinose) with subsequent introduction of the azide via the 4-O-triflate. Access to a corresponding β-azido ester was achieved in good yield. Little elimination product was observed by introduction of the azide via the 3-O-triflate. These azido esters are scaffolds, which may be predisposed to adopt secondary structural motifs, for example, for use as peptidomimetics; they may also be utilised for the preparation of stereodiverse compound libraries. |
| Keywords: | Sugar amino acids Peptidomimetics Scaffolds Gamma amino acids |
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