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Updated: Jun 28, 2026

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
Published on: October 19, 2017
Total synthesis of (-)-amathaspiramide F
Kazuhiko Sakaguchi1, Miki Ayabe, Yusuke Watanabe
1Graduate School of Science, Department of Material Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan. sakaguch@sci.osaka-cu.ac.jp
Abstract:
The stereoselective total synthesis of the marine alkaloid (-)-amathaspiramide F (1) was achieved from the alpha-hydoxy-alpha-ethynylsilane 2. The crucial steps in this synthesis involved not only the enolate Claisen rearrangement of the alpha-acyloxy-alpha-alkenylsilane 6 for the construction of the nitrogen-containing quaternary carbon center, but also the chemoselective formation of the azaspirohemiaminal 12 using heptamethyldisilazane as the methylamine equivalent and the regioselective dibromination of the phenol moiety of 12 using n-Bu(4)NBrCl(2).
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