Synthesis of the eastern portion of ajudazol a based on Stille coupling and double acetylene carbocupration.
[structure: see text] A strategy for the synthesis of ajudazol A, an unusual, pharmacologically active metabolite from myxobacteria, based on the Stille cross-coupling of a 2-stannyl-oxazole with a vinyl iodide unit is described; the vinyl halide unit containing a (Z,Z)-diene was prepared in one pot by the double acetylene carbocupration of a functionalized alkyl cuprate followed by trapping with 2,3-dibromopropene.
Krebs
Oliver
O
Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
Taylor
Richard J K
RJ
D000114:Acetylene / Q000737:chemistry*; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009231:Myxococcales / Q000737:chemistry; D013237:Stereoisomerism
D003374:Coumarins; C485090:ajudazol A; D000114:Acetylene