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α-acyliminium ion synthesis of elaeokanine B

✍ Scribed by Bernard P. Wijnberg; W.Nico Speckamp

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
193 KB
Volume
22
Category
Article
ISSN
0040-4039

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