Enantioselective synthesis of polycyclic carbocycles via an alkynylation-allylation-cyclization strategy.

Abstract

A new general three-stage strategy to access polycyclic ring systems bearing all-carbon quaternary centers with high enantioselectivity is reported. The required starting materials were readily accessed in racemic form through the α-alkynylation of ketoesters with EBX (EthynylBenziodoXolone) hypervalent iodine reagents. A Pd-catalyzed asymmetric decarboxylation allylation was then achieved in high yields and enantioselectivities with Trost's biphosphine ligands. Finally, transition-metal catalyzed cyclization of the obtained chiral enynes gave access to fused and spiro polycyclic ring systems constituting the core of many bioactive natural products.

DOI: 10.1021/ol5028333

Cite this paper

@article{Vita2014EnantioselectiveSO, title={Enantioselective synthesis of polycyclic carbocycles via an alkynylation-allylation-cyclization strategy.}, author={Maria Victoria Vita and Pascal Mi{\'e}ville and J{\'e}r{\^o}me Waser}, journal={Organic letters}, year={2014}, volume={16 21}, pages={5768-71} }