Synthesis of aryl-substituted derivatives of acetogenins using the Ti-catalyzed homo-cyclomagnesiation of 1,2-dienes as a key step.

New symmetric aryl-substituted derivatives of acetogenins were synthesized using the Ti-catalyzed homo-cyclomagnesiation of aryl-substituted 1,2-dienes at the key step. Ruthenium catalyzed oxidative cyclization of symmetric aryl-substituted 1Z,5Z-dienes was used to synthesize diols and ketols containing a tetrahydrofuran fragment. Diastereoselective reduction of ketols with L-selectride yielded target diols. In addition, by oxidation of ketols with Dess—Martin periodinane, diketones were synthesized in high yields. [ABSTRACT FROM AUTHOR]