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Synlett 2012(3): 371-374  
DOI: 10.1055/s-0031-1290135
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of Altenusin and Alterlactone

Judith Cudaj, Joachim Podlech*
Institut für Organische Chemie, Karlsruher Institut für Technologie (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)60847652; e-Mail: joachim.podlech@kit.edu;
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Publikationsverlauf

Received 27 October 2011
Publikationsdatum:
19. Januar 2012 (online)

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Abstract

The resorcylic lactone alterlactone, a mycotoxin produced by alternaria sp., was synthesized for the first time. The total synthesis was achieved in nine steps with 69% yield starting with acetal-protected phloroglucinic acid and 6-bromopiperonal, where the longest linear sequence consists of five steps. Key step is a ­Suzuki coupling used for the construction of the central biaryl bond. When the final deprotection with cleavage of benzyl ethers (yielding unprotected alterlactone) was performed in a less polar solvent the biaryl mycotoxin altenusin was obtained.

Key words

polyketides - fungal metabolites - resorcylic lactones - cross-coupling - Suzuki reaction

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