A total synthesis of the antitumour macrolide rhizoxin D |
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Authors: | Mitchell Ian S Pattenden Gerald Stonehouse Jeffrey |
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Institution: | School of Chemistry, The University of Nottingham, Nottingham, UK, NG7 2RD. |
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Abstract: | An enantioselective synthesis of rhizoxin D, isolated from the plant pathogenic fungus Rhizopus chinensis, is described. The overall strategy is based on elaboration of the delta-lactone-substituted vinyl stannane and the phosphonate-substituted vinyl iodide, followed by their coupling to the core 16-membered macrolide via a sequential intermolecular Horner-Wadsworth-Emmons olefination, leading to (50), and by an intramolecular Stille reaction. The triene oxazole-containing side chain in rhizoxin D is then introduced using the phosphine oxide in an E-selective Horner-Wittig reaction with the macrolide aldehyde. |
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