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Synlett 1999; 1999(10): 1624-1626
DOI: 10.1055/s-1999-2888
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Stereocontrolled Preparation of the C1-C14 Polyene Fragment of Benzenic Ansamycin Antibiotics Ansatrienin A and B

Kai-Uwe Schöning* , Rüdiger Wittenberg, Andreas Kirschning
  • *Institut für Organische Chemie der Technischen Universität Clausthal, Leibnizstraße 6, D-38678 Clausthal-Zellerfeld, Germany; Fax 5323-72 28 58; E-mail: andreas.kirschning@tu-clausthal.de
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Publication Date:
31 December 1999 (online)

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A practical synthesis of the C1-C14 polyene unit 5 in ansatrienin A (mycotrien I), 1a, and other ansamycin antibiotics is described which involves elaboration of the chiral unsaturated aldehyde 6 and phosphonate 7, followed by coupling of the building blocks by Horner-Emmons-olefination and Duthaler's aldolation. The synthesis of 6 successfully applies two consecutive Evans-aldol reactions for constructing the carbon backbone.

Evans-aldolation - Horner-Emmons olefination - macrolactam antibiotic