Highly Enantioselective 1,2-Addition of 2-[(Trimethylsilyl)oxy]furan to Aldehydes:  Application to Muricatacin Synthesis

Abstract

TMSOF 2-[(trimethylsilyl)oxy]furan has been used in an enantioselective aldol reaction for the first time. Indeed, addition of TMSOF to achiral aldehydes, in the presence ( R )-1,1‘-bi-2-naphthol (Binol), gave the 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 regards to the numerous multistep syntheses published so far) illustrated the efficiency of this strategy.