Department of Chemistry, Indian Institute of Technology Kanpur , Kanpur-208016, India.
J Org Chem. 2013 Oct 18;78(20):10106-20. doi: 10.1021/jo4013833. Epub 2013 Oct 1.
Dimeric indole alkaloids represent a structurally unique class of natural products having interesting biological activities. Recently, we reported the first total synthesis of flinderoles B and C, structurally unique and potent antimalarial natural products. Central to the design of the approach and by virtue of a one-pot, acid-catalyzed dimerization reaction, the route also provided total synthesis of the borreverine class of natural products. This full account details the progress of efforts that culminated in the protecting-group-free, six-step total synthesis of all of the flindersia alkaloids: dimethylisoborreverine, isoborreverine, flinderoles A-C, and their analogues. A biomimetic approach featuring a scalable and catalytic formal [3 + 2] cycloaddition and Diels-Alder reaction is outlined in detail. On the basis of the experimental observations, a detailed mechanism has been proposed for the dimerization of tertiary alcohol 28.
二聚吲哚生物碱是一类具有独特结构的天然产物，具有有趣的生物活性。最近，我们报道了结构独特的强效抗疟天然产物弗林德罗尔斯 B 和 C 的首次全合成。该方法的设计核心是通过一锅酸催化二聚反应，提供了硼替佐米类天然产物的全合成。本综述详细介绍了最终实现无保护基、六步全合成所有弗林德斯生物碱（二甲异波替林、异波替林、弗林德罗尔斯 A-C 及其类似物）的努力进展。详细概述了一种具有可扩展性和催化形式 [3+2] 环加成和 Diels-Alder 反应的仿生方法。基于实验观察，提出了二聚三级醇 28 的详细反应机理。
