Synthesis of a linear α-hydroxymethyl-pentapyrrole derivative and its cyclization to uroporphyrinogens

  • Okada K
  • Takakura H
  • Nomura K
 et al. 
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A linear pentapyrrole bearing α-hydroxymeythyl group in the terminal was synthesized by the stepwise coupling of α-free pyrrole with azafulvenium ion 6. When it was treated with a catalytic amount of p-toluensulfonic acid under anaerobic condition, followed by aerial oxidation of the products, a statistical mixture of uroporphyrin I-IV octamethyl esters was obtained. It is proposed that this transformation proceeds through a spiro-pyrrolenine as a key intermediate. (C) 2000 Elsevier Science Ltd.

Author-supplied keywords

  • Coupling reaction
  • Linear pentapyrrole derivatives
  • Rearrangement
  • Spiro- pyrrolenine intermediate

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  • Kunisuke Okada

  • Hiroyuki Takakura

  • Keishi Nomura

  • Kiyoshi Saburi

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