Condensed heteroaromatic ring systems. Part 24. Synthesis of rigidin, a pyrrolo [2, 3-d] pyrimidine marine alkaloid

…, Y Kondo, S Sato, H Yamanaka

Index: Sakamoto, Takao; Kondo, Yoshinori; Sato, Shuichiroh; Yamanaka, Hiroshi Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 5 p. 459 - 464

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Citation Number: 16

Abstract

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-methylbenzamide 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 ...