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Stereoselective cyclopropanation in the synthesis of 3'-deoxy-3'-C-hydroxymethyl-2',3'-methylene-uridine. 2014
Zofia Komsta, and
Benjamin A Mayes, and
Adel Moussa, and
Montserrat Shelbourne, and
Alistair Stewart, and
Andrew J Tyrrell, and
Laura L Wallis, and
Alexander C Weymouth-Wilson, and
Alexander Yurek-George
Idenix Pharmaceuticals, 320 Bent Street, Cambridge, Massachusetts 02141, United States.
The synthesis of the novel 2',3'-cyclopropane nucleoside 3'-deoxy-3'-C-hydroxymethyl-2',3'-methylene-uridine is described. Stereoselective construction of the cyclopropane ring was achieved via Simmons-Smith cyclopropanation of a benzyl protected silyl enol ether, which was itself derived from 1,2-O-isopropylidene-α-D-xylofuranose.
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