ol1021965_si_001.pdf (1.41 MB)
Expedient Enantioselective Synthesis of the Δ4-Oxocene Cores of (+)-Laurencin and (+)-Prelaureatin
journal contribution
posted on 2010-11-05, 00:00 authored by Jim Li, Judy M. Suh, Elbert ChinAn 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.