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Synthesis of α,β-Dehydrotryptophan by reaction of indole with the β-(N-methylamino)dehydroalanine derivative

✍ Scribed by Takashi Nakazawa; Masako Ishii; Hans-Jürgen Musiol; Luis Moroder

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 328 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10850-4

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✦ Synopsis

a,~Dehydrotryptophan 4 is synthesized by a sequence of readions starting with the comzpondiig serine derivative 1. This procedure includes substitution readion between indole and the methylamino group of the B(N-methylamioo)dehydroalanine derivative 3 in acetic acid. The key intermediate 3 is obtained by oxidation of 1 with diiethylsulfoxide activated by p-toluenesulfonyl chloride, followed by reaciion of the resulting ~-tosyldehydroserine 2 with methylamine.

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