Issue 31, 2012
From the journal:

RSC Advances

Synthesis of 6,6′-(S)-cyclo-2′-deoxyuridine featuring a unique Barbier-style cyclization†

Christopher S. Theilea  and  Larry W. McLaughlin*a  

* Corresponding authors

a Boston College, Department of Chemistry, Merkert Chemistry Center, 2609 Beacon Street Chestnut Hill, MA, USA
E-mail: larry.mclaughlin@bc.edu
Fax: +01 617 552 2705
Tel: +01 617 552 3622

Abstract

Here we present the synthesis of the novel nucleoside 6,6′-(S)-cyclo-2′-deoxyuridine (1). This efficient synthesis is carried out starting from 2′-deoxyuridine and reaches the deprotected product in few steps and high yield. Crystal structures of the product indicate that it is a very good structural mimic of thymidine as found in DNA duplexes. This rigidified nucleoside locks the uracil base in the anti conformation, positioning the nucleobase for Watson–Crick duplex formation at significant entropic savings. The structure of 6,6′-(S)-cyclo-2′-deoxyuridine maps more favorably onto naturally occurring nucleosides than previous cyclo nucleosides. The synthesis features a unique Barbier-style cyclization, expanding on Luche and Sarandeses allyl zinc additions, to create a 7-membered ring in good yield.

Graphical abstract: Synthesis of 6,6′-(S)-cyclo-2′-deoxyuridine featuring a unique Barbier-style cyclization

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Article information

DOI
https://doi.org/10.1039/C2RA21559D
Article type
Communication
Submitted
25 Jul 2012
Accepted
08 Oct 2012
First published
09 Oct 2012

RSC Adv., 2012,2, 11678-11680

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Synthesis of 6,6′-(S)-cyclo-2′-deoxyuridine featuring a unique Barbier-style cyclization

C. S. Theile and L. W. McLaughlin, RSC Adv., 2012, 2, 11678 DOI: 10.1039/C2RA21559D

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