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Radical Cyclization Cascades of Unsaturated Meldrum’s Acid Derivatives

By Brice Sautier (1305678), Sarah E. Lyons (2130712), Michael R. Webb (1688479) and David J. Procter (1298652)


Unsaturated, differentially substituted Meldrum’s acid derivatives undergo cascade cyclizations upon ester reduction with SmI<sub>2</sub>–H<sub>2</sub>O. The cascade cyclizations proceed in good yield and with high diastereocontrol and convert simple, achiral starting materials to complex molecular architectures, bearing up to four stereocenters, in a single operation. The cascades are triggered by the generation and trapping of unusual radical-anions formed by electron transfer to the ester carbonyl

Topics: Medicine, Microbiology, Cell Biology, Molecular Biology, Developmental Biology, Cancer, Infectious Diseases, Computational Biology, Environmental Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, generation, stereocenter, acid, DerivativesUnsaturated, diastereocontrol, transfer, carbonyl, cascade cyclizations, SmI, ester, derivative, material, achiral, electron, Radical Cyclization Cascades, Meldrum, differentially, Unsaturated
Year: 2012
DOI identifier: 10.1021/ol2029367.s001
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Provided by: FigShare
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