10.1021/ol1021965.s001
Jim Li
Jim
Li
Judy M. Suh
Judy M.
Suh
Elbert Chin
Elbert
Chin
Expedient Enantioselective Synthesis of the Δ<sup>4</sup>-Oxocene Cores of (+)-Laurencin and (+)-Prelaureatin
American Chemical Society
2010
sequence
stereoselective
vinylsilane
intramolecular
insertion
Laurencin
Core
laurencin
enantioselective synthesis
Prelaureatin
core
stereocontrolled cyclization
Expedient Enantioselective Synthesis
Oxocene
tetrahydrofuran precursors
silyl
regio
prelaureatin
fragmentation
oxocene
cascade
2010-11-05 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Expedient_Enantioselective_Synthesis_of_the_sup_4_sup_Oxocene_Cores_of_Laurencin_and_Prelaureatin/2716372
An expedient enantioselective synthesis of the Δ<sup>4</sup>-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.