Total synthesis of (-)-amathaspiramide F |
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Authors: | Sakaguchi Kazuhiko Ayabe Miki Watanabe Yusuke Okada Takuya Kawamura Kazushige Shiada Tetsuro Ohfune Yasufumi |
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Institution: | Graduate School of Science, Department of Material Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan. sakaguch@sci.osaka-cu.ac.jp |
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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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