title: Total synthesis of myxothiazols, novel bis-thiazole beta-methoxyacrylate-based anti-fungal compounds from myxobacteria.
abstract: Convergent total syntheses of myxothiazols A and Z are described. The syntheses are based on elaboration of the (S)-E,E-diene thioamide 22, conversion of 22 into the bis-thiazole 27 and Wittig reactions between 27c and the aldehyde 30. The substituted beta-methoxyacrylate aldehyde 30 was produced via an Evans asymmetric aldol protocol or via the 2H-pyran-2-one 31. An E-selective Wittig reaction between the ylide derived from the phosphonium salt 27c and the (+)-aldehyde 30 led to (+)-myxothiazol Z (1b), and a corresponding reaction with the (+/-)-acrylamide aldehyde 44 gave (+/-)-myxothiazol A (1a). Complementary studies led to synthesis of the ester 47b, corresponding to myxothiazol R and myxothiazol S.
authors.affiliation: School of Chemistry, University of Nottingham, University Park, UK.
authors.forename: John M
authors.initials: JM
authors.lastname: Clough
authors.forename: Henry
authors.initials: H
authors.lastname: Dube
authors.forename: Bruce J
authors.initials: BJ
authors.lastname: Martin
authors.forename: Gerald
authors.initials: G
authors.lastname: Pattenden
authors.forename: K Srinivasa
authors.initials: KS
authors.lastname: Reddy
authors.forename: Ian R
authors.initials: IR
authors.lastname: Waldron
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D008689:Methacrylates / Q000138:chemical synthesis / Q000494:pharmacology; D009231:Myxococcales / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000935:Antifungal Agents; D008689:Methacrylates; D013844:Thiazoles; C030517:myxothiazol