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Synthesis 2005(19): 3191-3192  
DOI: 10.1055/s-2005-918447
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of (S)-Gizzerosine - A Potent Inducer of Gizzard Erosion in Chicks - Using Successive Zinc-Mediated and Palladium-Catalyzed Coupling Reactions

Yasuharu Shimasakia, Hiromasa Kiyota*a, Minoru Satob, Shigefumi Kuwaharaa
a Division of Bioscience & Biotechnology for Future Bioindustry, Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiya, Aoba-ku, Sendai 981-8555, Japan
Fax: +81(22)7178783; e-Mail: kiyota@biochem.tohoku.ac.jp;
b Division of Biological Resource Science, Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiya, Aoba-ku, Sendai 981-8555, Japan
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Publication History

Received 15 September 2005
Publication Date:
25 October 2005 (online)

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Abstract

Gizzerosine, a potent inducer of gizzard erosion in chicks, was synthesized using successive zinc-mediated and palladium-catalyzed coupling reactions as the key steps. The piperonyl moiety was used as a novel N-protecting group.

Key words

gizzerosine - gizzard erosion - chickens - total synthesis - histamine