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Issue 35, 2015
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Regio- and stereoselective synthesis of 2′-β-substituted-fluoroneplanocin A analogues as potential anticancer agents

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Abstract

A series of 2′-β-substituted-6′-fluoro-cyclopentenyl-pyrimidines and -purines 8 and 9 were successfully synthesized from D-ribose in a regio- and stereoselective manner. The functionalization at the C2-position of 6′-fluoro-cyclopentenyl nucleosides was achieved via regioselective protection of a hydroxyl group at the C3-position and stereoselective formation of C2-triflate followed by direct SN2 reaction with a fluoro or azido nucleophile. All the synthesized compounds were evaluated for their anticancer activities in several tumor cell lines, but were found to be neither active nor toxic.

Graphical abstract: Regio- and stereoselective synthesis of 2′-β-substituted-fluoroneplanocin A analogues as potential anticancer agents

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Supplementary files

Article information


Submitted
03 Jul 2015
Accepted
21 Jul 2015
First published
22 Jul 2015

Org. Biomol. Chem., 2015,13, 9236-9248
Article type
Paper
Author version available

Regio- and stereoselective synthesis of 2′-β-substituted-fluoroneplanocin A analogues as potential anticancer agents

A. Nayak, P. K. Sahu, J. Song, S. K. Lee and L. S. Jeong, Org. Biomol. Chem., 2015, 13, 9236
DOI: 10.1039/C5OB01348H

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