HIGHLY ENANTIOSELECTIVE 1,2-ADDITION OF 2-[(TRIMETHYLSILYL)OXY]FURAN TO ALDEHYDES - APPLICATION TO MURICATACIN SYNTHESIS

TMSOF 2-[(trimethylsilyl)oxy]furan has been used in an enantioselectiv e aldol reaction far the first time. Indeed, addition of TMSOF to achi ral aldehydes, in the presence (R)-1,1'-bi-2-naphthol (Binol), gave th e corresponding butenolides with moderate diastereomeric ratios (dr = 60%) and ee's between 60 and 90%. Application of this reaction to the total synthesis of annonaceous muricatacin in only two steps (in regar ds to the numerous multistep syntheses published so far) illustrated t he efficiency of this strategy.