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

Edwards, Alison A. and Sanjayan, Gangadhar J. and Haschisu, Shuji and Soengas, Raquel and Stewart, Alistair and Tranter, George E. and Fleet, George W.J. (2006) Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships. Tetrahedron, 62 . pp. 4110-4119. ISSN 0040-4020. (Access to this publication is restricted)

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http://dx.doi.org/10.1016/j.tet.2006.02.007

Abstract

Templated tetrahydrofuran-based g-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 beta-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.

Item Type: Article
Subjects: Q Science
Q Science > QD Chemistry
Divisions: Faculties > Science Technology and Medical Studies > Medway School of Pharmacy
Depositing User: Alison Edwards
Date Deposited: 03 Sep 2008 22:30
Last Modified: 06 May 2014 08:58
Resource URI: http://kar.kent.ac.uk/id/eprint/4896 (The current URI for this page, for reference purposes)
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