Catalytic, asymmetric transannular aldolizations: Total synthesis of (+)-hirsutene
Catalytic, asymmetric transannular aldolizations: Total synthesis of (+)-hirsutene
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DOI：
10.1021/ja8024164
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发表时间：
2008-05-28
影响因子：
15
通讯作者：
List, Benjamin
中科院分区：
文献类型：
--
作者：
Chandler, Carley L.;List, Benjamin
我们报道了一种不对称催化的跨环缩醛反应，它提供了对天然产物合成有用的多环产物。我们发现，1，4-环辛二酮以较高的产率和较高的对映选择性催化了1，4-环辛二酮与相应的环β-羟基酮的跨环Aldol反应。我们的反应在(+)-水飞蓟烯的全合成中得到了证实。
We report an asymmetric, catalytic transannular aldolization that provides polycyclic products useful for natural product synthesis. We found that a proline-derivative catalyzes the transannular aldol reaction of 1,4-cyclooctanediones to the corresponding cyclic beta-hydroxy ketones in good yields and with high enantioselectivities. The utility of our reaction has been demonstrated in a total synthesis of (+)-hirustene.