Synthesis of new 2′, 3′-modified uridine derivatives from 2′,3′-ene-2′-phenylselenonyl uridine by Michael addition reactions

Abstract

The synthetic utilities of 2′,3′-ene-2′-phenylselenones 12 and 13 as synthetic equivalent of a dication [CH 2 +-CH 2 +] 5 have been demonstrated. They act as Michael acceptors, and undergo conjugate addition reactions at C-3′ with various sulfur, nitrogen, oxygen and carbon nucleophiles giving various C-3′ substituted-2,2′-O-anhydro-, or 2′,3′-ene-3′-substituted, or 2′,3′-fused nucleoside derivatives. Easy access to these 3′-substituted nucleosides from 2′,3′-ene-2′-phenylselenones 12 and 13 make them powerful complement to the corresponding 2′-substituted derivatives obtainable from 2′,3′-ene-3′-phenylselenonyl nucleoside 4 (ref. 72–74).