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Total synthesis of (±)-α-allokainic acid via two allylsilane N-acyliminium ion reactions

✍ Scribed by Hendrik H Mooiweer; Henk Hiemstra; W.Nico Speckamp

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
914 KB
Volume
47
Category
Article
ISSN
0040-4020

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✦ Synopsis

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 intramolecular allylsilane N-acyliinium ion reaction of 4. which closes the pyrrolidine ring by C4-C5 bond formation. Remarkably, the intramolecular variant of the coupling of 8 with 9 in order to prepare &lactone 5 failed to proceed.

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