C-Glycosides and C-disaccharide precursors through carbonylative Stille coupling reactions

Abstract

Under CO atmosphere and in the presence of Pd 2(dba) 3 and Ph 3As a suitably protected 1-stannylglucal derivative could be carbonylated and coupled to 5-bromo-7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives. The carbonylative Stille coupling was also successful between 1-iodoglucals and tributyl(vinyl)stannane or tributyl(fur-2-yl)stannane. A cross-conjugated dienone was also obtained through coupling of a 1-stannylglucal with a 1-iodoglucal derivative.