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Synthesis 2000; 2000(1): 144-148
DOI: 10.1055/s-2000-6219
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Convenient Synthesis and Conversion of a (Z)-α,β-Didehydroornithine Derivative to α,β-Didehydrokyotorphin

Yasuchika Yonezawa* , Takako Hirosaki, Takashi Hayashi, Chung-gi Shin
  • *Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan; Fax +81 (45) 4 91 79 15; E-mail: shin@cc.kanagawa-u.ac.jp
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Publication Date:
31 December 2000 (online)

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Hydrogenolysis of the azido group of methyl (Z)-2-(N-Cbz)amino-5-azidopent-2-enoate, derived by selective reduction and azidation of the side chain carboxyl group of N-protected (Z)-ΔGlu-OMe, gave (Z)-α,β-didehydroornithine derivative (7). The formed 7 was further converted to the basic (Z)-α,β-didehydroarginine and the acid containing (Z)-α,β-didehydrokyotorphin.

amines - azides - peptides - condensations - coupling - reductions - didehydroamino acids - didehydroornithine

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