The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation

John A. Enquist and Brian M. Stoltz ()
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John A. Enquist: The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, California Institute of Technology, 1200 East California Boulevard, MC164-30, Pasadena, California 91125, USA
Brian M. Stoltz: The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, California Institute of Technology, 1200 East California Boulevard, MC164-30, Pasadena, California 91125, USA

Nature, 2008, vol. 453, issue 7199, 1228-1231

Abstract: Complex synthesis: Doubling up The utility of a 'double catalytic enantioselective reaction' is demonstrated by the rapid protecting group-free synthesis of the diterpenoid (−)-cyanthiwigin F, a natural marine product originally isolated from the sea sponge Myrmekioderma styx. Double catalytic enantioselective reactions have the potential to construct stereochemically complex molecules in a single operation by creating several stereocentres at remote points within the same molecular scaffold. The key step in the nine-step synthesis of cyanthiwigin F is the conversion of a complicated mixture of racemic and meso diastereomers into a synthetically useful intermediate with exceptional enantiomeric excess.

Date: 2008
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DOI: 10.1038/nature07046

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