重新审视一种经典的阿朴菲生物碱合成方法：通过分子内施密特反应介导合成（+）-阿朴菲定。
Revisiting a classic approach to the Aspidosperma alkaloids: an intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine.
作者信息
Iyengar Rajesh, Schildknegt Klaas, Morton Martha, Aubé Jeffrey
机构信息
Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Room 4070, Malott Hall, University of Kansas, Lawrence, Kansas 66045-7582, USA.
出版信息
J Org Chem. 2005 Dec 23;70(26):10645-52. doi: 10.1021/jo051212n.
Abstract
[reaction: see text] A total synthesis of (+)-aspidospermidine (1) is described. The key reactions used in the synthesis of this pentacyclic Aspidosperma alkaloid were a deracemizing imine alkylation/Robinson annulation sequence, a selective "redox ketalization", and an intramolecular Schmidt reaction. A Fischer indolization step carried out on a tricyclic ketone mirrored the sequence reported by Stork and Dolfini in their classic aspidospermine synthesis.
摘要
[反应：见正文] 描述了（+）-阿朴菲啶（1）的全合成。该五环阿朴菲属生物碱合成中使用的关键反应是消旋亚胺烷基化/罗宾逊缩环序列、选择性“氧化还原缩酮化”和分子内施密特反应。在三环酮上进行的费歇尔吲哚化步骤反映了斯托克和多尔菲尼在其经典的阿朴菲明合成中报道的序列。
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