Route to Synthetic Analogues of Rocaglamide and Aglafoline using Cascade Transformations initiated by Oxy-Cope Rearrangement of Bis-Alkynes

Dr. Alabugin and his team have developed a method for preparing a cyclobutene compound or a cyclopentenone. The method comprises contacting an α,β-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.