The Knight route to cyclopiazonic acid: enantioselective synthesis of a key intermediate |
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Authors: | Christian Beyer Frank Sondermann Axel Figge |
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Affiliation: | Bergische Universität Wuppertal, Fachgruppe Chemie Gaußstraße 20, 42119 Wuppertal, Germany |
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Abstract: | The indole alkaloid α-cyclopiazonic acid (CPA) is one of the few known inhibitors of sarco(endo)plasmic reticulum Ca2+-ATPase (SERCA) besides thapsigargin and artemisinin. Inhibitors of SERCA hold promise as novel anticancer and antimalarial drugs. Since its structure elucidation three racemic syntheses of α-cyclopiazonic acid have been published. We report now the first enantioselective and high yielding synthesis of a key-intermediate of the Knight synthesis, currently the most efficient route to CPA. Our synthesis is based on a diastereoselective 1,4-cuprate addition followed by an enolate azidation of an indolylacrylic acid modified with the Evans auxiliary. |
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Keywords: | Indole alkaloid Cylopiazonic acid SERCA Key-intermediate Enantioselective synthesis Evans auxiliary |
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