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

✍ Scribed by Kunisuke Okada; Hiroyuki Takakura; Keishi Nomura; Kiyoshi Saburi

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
190 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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