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Issue 24, 2005
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A total synthesis of the antitumour macrolide rhizoxin D

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Abstract

An enantioselective synthesis of rhizoxin D (2), isolated from the plant pathogenic fungus Rhizopus chinensis, is described. The overall strategy is based on elaboration of the δ-lactone-substituted vinyl stannane 7 and the phosphonate-substituted vinyl iodide 9, followed by their coupling to the core 16-membered macrolide 6via 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 8 in an E-selective Horner–Wittig reaction with the macrolide aldehyde 51b.

Graphical abstract: A total synthesis of the antitumour macrolide rhizoxin D

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Publication details

The article was received on 27 May 2005, accepted on 07 Oct 2005 and first published on 15 Nov 2005


Article type: Paper
DOI: 10.1039/B507570J
Citation: Org. Biomol. Chem., 2005,3, 4412-4431
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    A total synthesis of the antitumour macrolide rhizoxin D

    I. S. Mitchell, G. Pattenden and J. Stonehouse, Org. Biomol. Chem., 2005, 3, 4412
    DOI: 10.1039/B507570J

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