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亚胺作为生物碱和新型氮杂环合成关键中间体的近期应用

Recent Applications of Imines as Key Intermediates in the Synthesis of Alkaloids and Novel Nitrogen Heterocycles.

作者信息

Martin Stephen F

机构信息

Department of Chemistry and Biochemistry, The University of Texas, Austin, TX 78712 USA.

出版信息

Pure Appl Chem. 2009;81(2):195-204. doi: 10.1351/PAC-CON-08-07-03.

DOI:10.1351/PAC-CON-08-07-03
PMID:20046937
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2723779/
Abstract

One of the major challenges in contemporary synthetic organic chemistry is the design and development of new tactics and strategies and their application to concise and efficient syntheses of biologically active natural products. Strategies that utilize reactions that enable the rapid assembly of the skeletal framework of such targets are thus especially attractive. In this context, we have developed novel applications of imine chemistry in Mannich and related reactions, cascade processes, and multicomponent reactions to rapidly assemble structural subunits common to diverse families of alkaloids. The practical utility of these chemistries is evidenced by their use in the execution of facile total syntheses of (±)-epilupinine (1), (±)-tashiromine (2), (-)-epimyrtine (3), and (±)-roelactamine (4) as well as other nitrogen heterocycles of potential biological interest.

摘要

当代有机合成化学面临的主要挑战之一是设计和开发新的策略及其应用于简洁高效地合成生物活性天然产物。因此，利用能够快速组装此类目标骨架结构的反应的策略特别有吸引力。在此背景下，我们开发了亚胺化学在曼尼希反应及相关反应、串联反应和多组分反应中的新应用，以快速组装不同生物碱家族共有的结构亚基。这些化学方法的实用性体现在它们被用于轻松全合成（±）-表鲁平宁（1）、（±）-塔希罗明（2）、（-）-表桃金娘碱（3）和（±）-罗勒酰胺（4）以及其他具有潜在生物学意义的氮杂环化合物。

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