Cytotoxic Amphidinin B Synthesized

  • Author: Brigitte Osterath
  • Published Date: 18 December 2010
  • Source / Publisher: European Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Cytotoxic Amphidinin B Synthesized

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The compound Amphidinin B could become a new co-player in fighting cancer. Indian researchers have synthesized the linear polyketide at a gram-scale and showed that it kills breast cancer cells very efficiently.

Amphidinin B is found in the dinoflagellate Amphidinium, a single-celled marine creature. Up to now, the substance’s biological properties could not be tested as the available amounts were too low. Jhillu S. Yadav and his co-workers at Indian Institute of Chemical Technology in Hyderabad have now changed that by developing a stereoselective total synthesis.

Construction of the key, substituted tetrahydrofuran moiety was achieved by Sharpless asymmetric epoxidation, base-induced epoxide ring-opening, radical cyclization, diastereoselective reduction of the exo-cyclic double bond, one-pot allylation followed by debenzylation, Evans alkylation, and Yamaguchi esterification.

Images: (c) Wiley-VCH

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Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH