NEW ROUTE TO SYNTHETIC ANALOGUES OF ROCAGLAMIDE AND AGLAFOLINE USING CASCADE TRANSFORMATIONS INITIATED BY OXY-COPE REARRANGEMENTS OF BIS-ALKYNES

摘要

A method for preparing a cyclobutene compound or a cyclopentenone is provided. The method comprises contacting an a,ß-diketone with a metal acetylide at a temperature below 0°C to thereby form a reaction mixture comprising a bis-alkyne precursor. The bis-alkyne precursor rearranges into a bis-allenic intermediate, which undergoes further rearrangement into the cyclobutene compound or the cyclopentenone compound as the temperature of the reaction mixture increases from below 0°C to above 0°C.