Enantioselective Synthesis of Polycyclic Carbocycles via an Alkynylation-Allylation-Cyclization Strategy

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 alpha-alkynylation of ketoesters with EBX (EthynylBenziodoXolone) hypervalent iodine reagents. A Pd-catalyzed asymmetric decarboxylation allylation was then achieved in high yields and enantioselectivities with Trosts 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.


Published in:
Organic Letters, 16, 21, 5768-5771
Year:
2014
Publisher:
Washington, American Chemical Society
ISSN:
1523-7060
Laboratories:




 Record created 2014-12-30, last modified 2018-03-17

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