Total synthesis of (卤)-antofine
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- 作者：Ming Yi ; Peiming Gu ; Xiao-Yan Kang ; Jian Sun ; Rui Li ; Xue-Qiang Li
- 关键词：Synthesis ; Alkaloids ; Antofine ; Schmidt reaction ; Horner&ndash ; Wadsworth&ndash ; Emmons reaction
- 刊名：Tetrahedron Letters
- 出版年：1 January, 2014
- 年：2014
- 卷：55
- 期：1
- 页码：105-107
- 全文大小：472 K
文摘
An efficient preparation of (卤)-antofine is described. The main steps involved in this synthesis are the Horner-Wadsworth-Emmons reaction, the intramolecular Schmidt reaction of an azido aldehyde, and the one-pot deprotection of the N-formyl group, followed by Pictet-Spengler cyclization. The asymmetric hydrogenation of the trisubstituted 伪,尾-unsaturated ester is also explored, however only moderate enantio-control (55% ee) is obtained. Finally, (卤)-antofine is prepared in six steps from the phenanthryl aldehyde 5 with an overall yield of 35%.