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Synlett 1999; 1999(S1): 901-904
DOI: 10.1055/s-1999-3105
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Total Synthesis of (±)-Phytochromobilin Starting from Two Pyrrole Derivatives

Takashi Kakiuchi* , Hideki Kinoshita, Katsuhiko Inomata
  • *Department of Chemical Science, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan; Fax +81(76)2 64 57 42; E-mail: inomata@cacheibm.s.kanazawa-u.ac.jp
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Publication Date:
31 December 1999 (online)

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(±)-Phytochromobilin was synthesized as an acid form by developing a convenient method for the preparation of A- and D-rings starting from a 2-tosylpyrrole derivative, followed by efficient construction of A/B- and C/D-ring components via Wittig-type coupling reaction of 5-tosylpyrrolinones with 2-formylpyrrole, and palladium catalyzed deprotection of allyl esters of propanoic acid side chains of C-8 and C-12.

phytochrome - tetrapyrrole - phytochromobilin - total synthesis - transformation of pyrroles