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Synthesis 2000; 2000(2): 214-216
DOI: 10.1055/s-2000-6246
short paper
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A Short Synthesis of Optically Active γ,γ-Dimethylallyltryptophan (DMAT)

Hidemasa Hikawa* , Yuusaku Yokoyama, Yasuoki Murakami
  • *School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan; Fax +81 (47) 4 72 15 89; E-mail: yokoyama@phar.toho-u.ac.jp
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Publikationsdatum:
31. Dezember 2000 (online)

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A short synthesis (4 steps) of optically active γ,γ-dimethylallyltryptophan (1, DMAT) was accomplished from N α-tert-butoxycarbonyl(Boc)-4-(3-hydroxy-3-methyl-1-buten-1-yl)-1-tosyl-tryptophan methyl ester (5) prepared by Heck reaction of N α-Boc-4-bromo-1-tosyltryptophan methyl ester (4) with 1,1-dimethylallylalcohol.

4-bromotryptophan - γ,γ-dimethylallyltryptophan (DMAT) - optically active synthesis - Heck reaction