Enantioselective Highly Efficient Synthesis of (−)-Cephalotaxine Using Two Palladium-Catalyzed Transformations
Enantioselective Highly Efficient Synthesis of (−)-Cephalotaxine Using Two Palladium-Catalyzed Transformations
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DOI：
10.1021/ja991650
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发表时间：
1999-10
影响因子：
15
通讯作者：
Lutz F. Tietze and;H. Schirok
中科院分区：
文献类型：
--
作者：
Lutz F. Tietze and;H. Schirok
三尖杉碱(1)是从三尖杉属植物中分离得到的主要生物碱，由于其几个衍生物具有良好的抗肿瘤活性和独特的结构特征而引起了人们的极大关注。在这里，我们描述了一种高效的1的对映选择性合成方法，从25开始，通过两次连续的Pd催化转化得到五环产物6。25中的控制立体中心是通过烯酮16的对映选择性还原引入的。
Cephalotaxine (1), the major alkaloid isolated from Cephalotaxus species, has attracted considerable attention due to the promising antitumor activity of several of its derivatives and its unique structural features. Herein we describe a highly efficient enantioselective synthesis of 1 employing two successive Pd-catalyzed transformations starting from 25 to give the pentacyclic product 6. The controlling stereogenic center in 25 was introduced by an enantioselective reduction of the enone 16.