Organic Letters 2005-03-17

Synthesis of the eastern portion of ajudazol a based on Stille coupling and double acetylene carbocupration.

Oliver Krebs, Richard J K Taylor

Index: Org. Lett. 7 , 1063, (2005)

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Abstract

[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.