A total synthesis of the antitumour macrolide rhizoxin D.
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.
Mitchell
Ian S
IS
School of Chemistry, The University of Nottingham, Nottingham, UK, NG7 2RD.
Pattenden
Gerald
G
Stonehouse
Jeffrey
J
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000737:chemistry*; D015394:Molecular Structure
D000970:Antineoplastic Agents; D007783:Lactones; D018942:Macrolides; C479980:rhizoxin D