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

Takao Sakamoto, Yoshinori Kondo, Shuichiroh Sato, Hiroshi Yamanaka

Research output: Contribution to journalArticle

16 Citations (Scopus)

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-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.

Original languageEnglish
Pages (from-to)459-464
Number of pages6
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number5
DOIs
Publication statusPublished - 1996 Mar 7

ASJC Scopus subject areas

  • Chemistry(all)

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