TY - JOUR
T1 - Condensed heteroaromatic ring systems. Part 24. Synthesis of rigidin, a pyrrolo[2,3-d]pynmidine marine alkaloid
AU - Sakamoto, Takao
AU - Kondo, Yoshinori
AU - Sato, Shuichiroh
AU - Yamanaka, Hiroshi
PY - 1996/3/7
Y1 - 1996/3/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0002233570&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0002233570&partnerID=8YFLogxK
U2 - 10.1039/p19960000459
DO - 10.1039/p19960000459
M3 - Article
AN - SCOPUS:0002233570
SN - 1470-4358
SP - 459
EP - 464
JO - Journal of the Chemical Society. Perkin Transactions 1
JF - Journal of the Chemical Society. Perkin Transactions 1
IS - 5
ER -
