对 (-)-palau'amine、(-)-axinellamines 和 (-)-massadines 的对映选择性全合成。
Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.
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
J Am Chem Soc. 2011 Sep 21;133(37):14710-26. doi: 10.1021/ja2047232. Epub 2011 Aug 23.
Abstract
Dimeric pyrrole-imidazole alkaloids represent a rich and topologically unique class of marine natural products. This full account will follow the progression of efforts that culminated in the enantioselective total syntheses of the most structurally ornate members of this family: the axinellamines, the massadines, and palau'amine. A bio-inspired approach capitalizing on the pseudo-symmetry of the members of this class is recounted, delivering a deschloro derivative of the natural product core. Next, the enantioselective synthesis of the chlorocyclopentane core featuring a scalable, catalytic, enantioselective Diels-Alder reaction of a 1-siloxydiene is outlined in detail. Finally, the successful divergent conversion of this core to each of the aforementioned natural products, and the ensuing methodological developments, are described.
摘要
二聚吡咯并咪唑生物碱是一类具有丰富结构和拓扑独特性的海洋天然产物。本综述将介绍一系列研究工作的进展，这些工作最终实现了该家族中结构最为复杂的成员：轴突素、马萨丁和 palau'amine 的对映选择性全合成。本研究报告了一种基于该类化合物的拟对称性的生物启发方法，得到了天然产物核心的去氯衍生物。接下来，详细描述了具有可扩展、催化和对映选择性的 Diels-Alder 反应的氯环戊烷核心的对映选择性合成，该反应使用了 1-硅氧二烯。最后，描述了该核心成功地转化为上述每种天然产物的发散转化，以及随之而来的方法学发展。
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本文引用的文献
1
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Angew Chem Int Ed Engl. 1998 Aug 17;37(15):2046-2067. doi: 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L.
2
Extending Pummerer reaction chemistry: studies in the palau'amine synthesis area.扩展 Pummerer 反应化学：在 palau'amine 合成领域的研究。
J Org Chem. 2011 Jun 17;76(12):5042-60. doi: 10.1021/jo200740b. Epub 2011 May 25.
3
Protecting-group-free synthesis as an opportunity for invention.无保护基合成：发明的机遇
Nat Chem. 2009 Jun;1(3):193-205. doi: 10.1038/nchem.216.
4
Practical C-H functionalization of quinones with boronic acids.醌与硼酸的实用 C-H 官能化。
J Am Chem Soc. 2011 Mar 16;133(10):3292-5. doi: 10.1021/ja111152z. Epub 2011 Feb 22.
5
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6
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J Org Chem. 2010 Jul 16;75(14):4657-73. doi: 10.1021/jo1006812.
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