Expedient Enantioselective Synthesis of the Δ4-Oxocene Cores of (+)-Laurencin and (+)-Prelaureatin

2010-11-05T00:00:00Z (GMT) by Jim Li Judy M. Suh Elbert Chin
An expedient enantioselective synthesis of the Δ4-oxocene cores present in (+)-laurencin and (+)-prelaureatin was accomplished in eight steps via a novel one-pot regio- and stereoselective ring cyclization−fragmentation−expansion cascade from the tetrahydrofuran precursors which were prepared by stereocontrolled cyclization from vinylsilanes. This process is highlighted by an intramolecular oxo-carbenoid insertion and a β-silyl fragmentation sequence.