A highly efficient aldehyde-olefin metathesis catalysed by the carbocation, 4-phenylphenyl-diphenylmethylium ion, has been developed. This protocol is characterized by high yields, low catalyst loading (down to 2 mol%), good functional group compatibility and mild reaction conditions.
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Carbocation catalysed ring closing aldehyde-olefin metathesis.
Chem Commun (Camb)
November 2018
Department of Chemistry, Organic Chemistry, Royal Institute of Technology (KTH), Teknikringen 30, SE-100 44 Stockholm, Sweden.
A highly efficient aldehyde-olefin metathesis catalysed by the carbocation, 4-phenylphenyl-diphenylmethylium ion, has been developed. This protocol is characterized by high yields, low catalyst loading (down to 2 mol%), good functional group compatibility and mild reaction conditions.
View Article and Find Full Text PDFTotal syntheses of cyanthiwigins B, F, and G.
Chemistry
August 2011
The Arnold and Mable Beckman Laboratories of Chemical Synthesis Department of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Blvd., MC 101-20, Pasadena, CA 91125, USA.
A concise and versatile approach toward the preparation of the cyanthiwigin family of cyathane natural products is described. By leveraging a unique double asymmetric catalytic alkylation procedure it is possible to quickly establish two of the most critical stereocenters of the cyanthiwigin framework with high levels of selectivity and expediency. The synthetic route additionally employs both a tandem ring-closing cross-metathesis reaction, and an aldehyde-olefin radical cyclization process, in order to rapidly arrive at the tricyclic cyathane core of the cyanthiwigin molecules.
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