Issue 6, 2014

A problem solving approach for the diastereoselective synthesis of (5′S)- and (5′R)-5′,8-cyclopurine lesions

Abstract

A short, efficient and high-yielding approach for the diastereoselective syntheses of the four (5′S)- and (5′R)-5′,8-cyclopurine lesions and their phosphoramidites has been developed. The intermediates prepared by these synthetic pathways provide an easy access to those modified nucleosides that constitute an important molecular library for recognition of DNA damage. With respect to previous synthesis, the key methodologies for cyclization steps and phosphoramidite synthesis were ameliorated.

Graphical abstract: A problem solving approach for the diastereoselective synthesis of (5′S)- and (5′R)-5′,8-cyclopurine lesions

Supplementary files

Article information

Article type
Research Article
Submitted
03 Cax 2014
Accepted
04 Qas 2014
First published
04 Qas 2014

Org. Chem. Front., 2014,1, 698-702

A problem solving approach for the diastereoselective synthesis of (5′S)- and (5′R)-5′,8-cyclopurine lesions

C. Chatgilialoglu, C. Ferreri, A. Masi, A. Sansone, M. A. Terzidis and M. Tsakos, Org. Chem. Front., 2014, 1, 698 DOI: 10.1039/C4QO00133H

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