通过高效酶促去对称化过程对（-）-别育亨烷和（-）-育亨烷进行对映选择性合成。
Enantioselective Syntheses of (-)-Alloyohimbane and (-)-Yohimbane by an Efficient Enzymatic Desymmetrization Process.
作者信息
Ghosh Arun K, Sarkar Anindya
机构信息
Department of Chemistry and Department of Medicinal Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana, 47906 (USA).
出版信息
European J Org Chem. 2016 Dec;2016(36):6001-6009. doi: 10.1002/ejoc.201601171. Epub 2016 Nov 28.
Abstract
Enantioselective syntheses of (-)-alloyohimbane and (-)-yohimbane was accomplished in a convergent manner. The key step involved a modified mild protocol for the enantioselective enzymatic desymmetrization of -diacetate. The protocol provided convenient access to an optically active monoacetate in multi-gram scale in high enantiomeric purity. This monoacetate was converted to (-)-alloyohimbane. Reductive amination of the derived aldehyde causes the isomerization leading to the -product and allows the synthesis of (-)-yohimbane.
摘要
以汇聚方式完成了(-)-别育亨烷和(-)-育亨烷的对映选择性合成。关键步骤涉及一种改进的温和方案，用于对二乙酸酯进行对映选择性酶促去对称化。该方案提供了一种便捷的方法，能够以多克规模、高对映体纯度获得光学活性单乙酸酯。这种单乙酸酯被转化为(-)-别育亨烷。衍生醛的还原胺化导致异构化生成α-产物，并实现了(-)-育亨烷的合成。
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