豪胺A的全合成：茚并四氢吡啶核心结构
Total synthesis of haouamine A: the indeno-tetrahydropyridine core.
作者信息
Burns Noah Z, Jessing Mikkel, Baran Phil S
机构信息
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
出版信息
Tetrahedron. 2009 Aug 15;65(33):6600-6610. doi: 10.1016/j.tet.2009.05.075.
Abstract
A full account of synthetic efforts towards the indeno-tetrahydropyridine core of haouamine A is presented. Initial failed strategies led to the unexpected discovery of a mild abnormal Chichibabin pyridine synthesis and provided knowledge and inspiration for the development of a cascade annulation that has enabled rapid and scalable access to the core in either racemic or enantiopure form.
摘要
本文全面介绍了针对豪胺A的茚并四氢吡啶核心结构的合成研究。最初失败的策略意外地促成了温和的异常齐齐巴宾吡啶合成反应的发现，并为级联环化反应的开发提供了知识和灵感，该反应能够以消旋或对映体纯的形式快速且可扩展地合成该核心结构。
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本文引用的文献
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2
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J Org Chem. 2009 Mar 20;74(6):2624-6. doi: 10.1021/jo802787j.
3
Calculated chemical shifts as a fine tool of conformational analysis: an unambiguous solution for haouamine alkaloids.计算化学位移作为构象分析的精细工具：豪胺生物碱的明确解决方案。
J Org Chem. 2008 Aug 1;73(15):5723-31. doi: 10.1021/jo702766x. Epub 2008 Jul 3.
4
Formal total synthesis of (-)-haouamine A.(-)-豪胺A的形式全合成。
Chem Commun (Camb). 2008 Jul 7(25):2870-2. doi: 10.1039/b805295f. Epub 2008 Jun 2.
5
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Nature. 2008 Jan 24;451(7177):417-24. doi: 10.1038/nature06485.
6
On the origin of the haouamine alkaloids.关于豪胺生物碱的起源
Angew Chem Int Ed Engl. 2008;47(1):205-8. doi: 10.1002/anie.200704576.
7
Biogenetic hypothesis and first steps towards a biomimetic synthesis of haouamines.
Chem Commun (Camb). 2007 Feb 21(7):719-21. doi: 10.1039/b613737g. Epub 2006 Dec 19.
8
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