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  • Title: Enantioselective synthesis of polycyclic carbocycles via an alkynylation-allylation-cyclization strategy.
    Author: Vita MV, Mieville P, Waser J.
    Journal: Org Lett; 2014 Nov 07; 16(21):5768-71. PubMed ID: 25315421.
    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.
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