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The total synthesis of α-allokainic acid

✍ Scribed by George A. Kraus; Jon O. Nagy

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
164 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

The aminoacid a-allokainic acid was synthesized in eight steps from thiazolidine 2. The aminoacid a-allokainic acid (1) was isolated from the marine algae Digenea sinlplex Ag.' Other members of this class include a-kainic acid,2 an isomer of 1 in which the isopropenyl and the acetic acid groups are cis, and domoic acid.3 Although 1 shows HD2CCH2 $--; h H02C 1" N CI 1 a-kainic acid domoic acid antihelmintic properties, its potent neurophysiological activity in mammals4 has attracted considerably more attention. Earlier syntheses were nonstereospecific but served to elucidate the structure. Recently, Oppolzer has communicated an elegant synthesis of 1 based on an intramolecular ene reaction. 5

We recently reported a 1,3-cycloaddition route that produced the functionalized pyrrolidine 2 and demonstrated that the cycloaddition was stereospecific.

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✍ Hendrik H Mooiweer; Henk Hiemstra; W.Nico Speckamp 📂 Article 📅 1991 🏛 Elsevier Science 🌐 French ⚖ 914 KB

A total synthesis of racemic a-allokainic acid is described, which starts from allylsilane 8 and methoxy-or chloroglycine derivative 9, and proceeds fully stereoselectively in nine steps and 1.1% overall yield. Key steps are the intermolecular N-acyliminium ion coupling of 8 with 9 and an intramolec

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Neuroexcitatory natural products are accessible from 1 via the intermediate 2, which is obtained by Ni-catalyzed cyclization, transposition of the protecting group, and Pd-catalyzed reduction with allylic transposition. This stepwise formation of stereocenters allows a highly direct and stereoselect