使用不对称烯丙基化反应对（+）-戈尼他胺、（+）-戈尼他胺氧化物和7,8-双表戈尼他胺进行从头不对称合成。
De Novo Asymmetric Syntheses of (+)-Goniothalamin, (+)-Goniothalamin oxide and 7,8-Bis-epi-Goniothalamin using Asymmetric Allylations.
作者信息
Harsh Philip, O'Doherty George A
机构信息
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506.
出版信息
Tetrahedron. 2009 Jun 27;65(26):5051-5055. doi: 10.1016/j.tet.2009.03.097.
Abstract
A highly enantio- and diastereoselective approach to either enantiomer of (+)-goniothalamin, (+)-goniothalamin oxide and 7,8-bis-epi-goniothalamin oxide has been developed from achiral cinnamyl alcohol or cinnamaldehyde. The asymmetry of the synthesis was installed by means of a Krische or Leighton allylation. The remaining stereochemistry was installed by a diastereoselective epoxidation.
摘要
已开发出一种从非手性肉桂醇或肉桂醛出发，以高度对映体和非对映体选择性的方法合成（+） - 角鲨胺、（+） - 角鲨胺氧化物和7,8 - 双表 - 角鲨胺氧化物的任一对映体。合成中的不对称性通过克里斯（Krische）或莱顿（Leighton）烯丙基化反应引入。其余的立体化学结构通过非对映选择性环氧化反应构建。
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