Development and application of a convergent strategy for the total synthesis of polycyclic ether natural products

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作者：
Sasaki, Makoto [1 ]
机构：
[1] Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan
来源：
Bulletin of the Chemical Society of Japan | 2007年 / 80卷 / 05期
关键词：
The polycyclic ether class of marine natural products presents formidable and challenging synthetic targets due to their structural complexity and exceptionally potent biological activities. Over the past decade; however; their extremely limited availability from natural sources has precluded detailed biological studies on polycyclic ethers. Therefore; the supply of useful quantities of these natural products by chemical total synthesis has been strongly demanded. We developed a highly convergent strategy for the rapid assembly of a huge polycyclic ether array; which features Suzuki-Miyaura cross-coupling reaction of alkylboranes; generated from exocyclic enol ethers; with cyclic ketene acetal triffates or phosphates combined with reductive ring-closure. The utility of this strategy was demonstrated by its application to the convergent total synthesis of the natural products gambierol and gymnocin-A. These practical synthetic routes allowed for the first time systematic studies of the structure-activity relationships of the polycyclic ether class of natural products. © 2007 The Chemical Society of Japan;
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页码：856 / 871
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