Concise syntheses of the cruciferous phytoalexins brassilexin, sinalexin, wasalexins, and analogues: expanding the scope of the vilsmeier formylation.
Efficient syntheses of the phytoalexins brassilexin, sinalexin, and analogues are demonstrated through the application of the Vilsmeier formylation to indoline-2-thiones followed by a new aqueous ammonia workup procedure. Similarly, a very concise two-pot synthesis of the phytoalexins wasalexins using sequential formylation-amination of indolin-2-ones is described. Remarkably, this novel aqueous ammonia workup allows the sequential one-pot formylation-amination, expanding substantially the scope of the Vilsmeier formylation of both indoline-2-thiones and indolin-2-ones. The examination of the formylation-amination reaction and optimization of conditions, as well as the syntheses and antifungal activities of several brassilexin analogues, are reported.
Pedras
M Soledade C
MS
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon SK S7N 5C9, Canada. soledade.pedras@usask.ca
Jha
Mukund
M
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D005561:Formates / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis*; D008826:Microbial Sensitivity Tests; D003904:Mitosporic Fungi / Q000187:drug effects; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010936:Plant Extracts / Q000138:chemical synthesis*; D012717:Sesquiterpenes; D013729:Terpenes; D013844:Thiazoles / Q000138:chemical synthesis*; D000094162:Phytoalexins
D000935:Antifungal Agents; D005561:Formates; D007211:Indoles; D010936:Plant Extracts; D012717:Sesquiterpenes; D013729:Terpenes; D013844:Thiazoles; C430120:sinalexin; C430121:brassilexin; D000094162:Phytoalexins