The marine alkaloid rigidin has been synthesized from 2,4-dimethoxy-7-phenylsulfonylpyrrolo[2,3-d]-pyrimidine. Lithiation of the pyrrolo[2,3-d]pyrimidine followed by electrophilic substitution with N,4-dimethoxy-N-methylbenzainide afforded a 6-(4-methoxy)benzoyl derivative which by alkaline hydrolysis and subsequent iodination was converted into 2,4-dimethoxy-5-iodopyrrolo[2,3-d]pyrimidin-6-yl 4-methoxyphenyl ketone. The palladium-catalysed arylation of this with 2-(4-methoxyphenyl)-1,3,2-dioxaborinane followed by demethylation with boron tribromide gave rigidin.
|Number of pages||6|
|Journal||Journal of the Chemical Society - Perkin Transactions 1|
|Publication status||Published - 1996 Mar 7|
ASJC Scopus subject areas