Dinuclear asymmetric Zn aldol additions: Formal asymmetric synthesis of fostriecin
Dinuclear asymmetric Zn aldol additions: Formal asymmetric synthesis of fostriecin
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DOI：
10.1021/ja042435i
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发表时间：
2005-03-23
影响因子：
15
通讯作者：
Shireman, BT
中科院分区：
文献类型：
--
作者：
Trost, BM;Frederiksen, MU;Shireman, BT
直接不对称羟醛缩合反应是高效合成复杂天然产物的有效方法。在这里，我们首次报道了我们最近报道的双核锌催化的炔基酮与醛的直接羟醛加成反应在一种有效的环状毒性天然产物福斯特列星的短而有效的不对称合成中的应用。这项工作不仅强调了Aldol方法的威力，而且强调了酰基硅烷Aldol加合物的实用性，因为它随后被用于乙烯基硅烷交叉偶联反应，该反应以8.5%的总收率为目标分子提供了14步最长的线性序列。
Direct asymmetric aldol reactions constitute a powerful methodology for the efficient synthesis of complex natural products. Herein we report the first application of our recently reported dinuclear Zn-catalyzed direct aldol addition of alkynyl ketones to aldehydes in a short and efficient formal asymmetric synthesis of fostriecin, a potent cyctotoxic natural product. This work highlights not only the power of the aldol methodology but also the utility of the akynyl silane aldol adducts, as it is subsequently utilized in a vinyl silane cross-coupling reaction which affords the target molecule in 14 steps for the longest linear sequence in 8.5% overall yield.