Total Synthesis of (−)-Amathaspiramide F

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• 作者：Kazuhiko Sakaguchi ; Miki Ayabe ; Yusuke Watanabe ; Takuya Okada ; Kazushige Kawamura ; Tetsuro Shiada ; Yasufumi Ohfune
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：December 4, 2008
• 年：2008
• 卷：10
• 期：23
• 页码：5449-5452
• 全文大小：170K
• 年卷期：v.10,no.23(December 4, 2008)
• ISSN：1523-7052

文摘

The stereoselective total synthesis of the marine alkaloid (−)-amathaspiramide F (1) was achieved from the α-hydoxy-α-ethynylsilane 2. The crucial steps in this synthesis involved not only the enolate Claisen rearrangement of the α-acyloxy-α-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-Bu₄NBrCl₂.