Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships

Journal article

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. © 2006 Elsevier Ltd. All rights reserved.

Authors: Edwards, A; Sanjayan, G; Hachisu, S; Soengas, R; Stewart, A

• Publication status: Published
• Journal: TETRAHEDRON
• Volume: 62
• Issue: 17
• Pages: 4110-4119
• Publication date: 2006-04-24
• DOI: 10.1016/j.tet.2006.02.007
• ISSN: 0040-4020
• Language: English
• Keywords: sugar amino acids; scaffolds; peptidomimetics; gamma amino acids