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