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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).

Citation

Kazuhiko Sakaguchi, Miki Ayabe, Yusuke Watanabe, Takuya Okada, Kazushige Kawamura, Tetsuro Shiada, Yasufumi Ohfune. Total synthesis of (-)-amathaspiramide F. Organic letters. 2008 Dec 4;10(23):5449-52

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PMID: 18973331

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