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[3]Dendralenes: Synthesis, Reactivity Studies and Employment in Diversity-Oriented Synthesis of Complex Polycyclic Scaffolds
Synlett ( IF 2 ) Pub Date : 2017-12-11 , DOI: 10.1055/s-0036-1590960
Sunil Ghosh 1, 2 , Gonna Naidu 1, 2 , Rekha Singh 1
Affiliation  

[3]Dendralenes are exquisite molecules as they exhibit enormous potential for the rapid generation of architecturally esoteric scaffolds when subjected to tandem Diels–Alder reactions, but their synthesis is a tall order. In conjunction with diversity-oriented synthesis, [3]dendralenes satisfy the potential demand for simultaneous and efficient synthesis of intricate collections of molecules that exhibit a range of activities for lead generation in drug discovery. This account chronicles our roller-coaster journey and systematic approach beginning from the synthesis of extremely unstable, non-isolable [3]dendralenes through moderately stable examples and then finally, highly functionalized, stable [3]dendralenes via sequential methylenation (using dimethylsulfonium methylide) and Horner–Wadsworth–Emmons olefination. It also describes the study of the attributes affecting their stability and reactivity with various dienophiles. In addition, it reports on how these dendralenes, upon astute maneuvering, can be engaged in a diene-transmissive Diels–Alder (DTDA) sequence, thus harnessing their full potential by construction of a small but diverse library of complex frameworks in a quick and efficient manner, with step and atom economy. 1 Introduction 2 Literature Methods for [3]Dendralene Synthesis 3 Our Tryst with [3]Dendralenes 3.1 Serendipitous Olefination with the Corey–Chaykovsky Ylide 3.2 Synthesis of [3]Dendralenes and Reactivity/Stability Studies 3.3 Diels–Alder Reactions of [3]Dendralenes 3.4 Tuning of [3]Dendralenes for the DTDA Reactions 3.5 Diversity-Oriented Synthesis with [3]Dendralenes 3.6 Rationalization of Factors Governing the Stability and Reactivity of [3]Dendralenes 4 Conclusions

中文翻译:

[3]Dendralenes:复杂多环支架的多样性导向合成中的合成、反应性研究和应用

[3] 树枝烯是一种精致的分子,因为它们在进行串联 Diels-Alder 反应时表现出快速生成结构深奥的支架的巨大潜力,但它们的合成是一项艰巨的任务。结合面向多样性的合成,[3]dendralenes 满足了同时有效合成复杂分子集合的潜在需求,这些分子集合在药物发现中表现出一系列的先导生成活性。该帐户记录了我们的过山车之旅和系统方法,从合成极其不稳定、不可分离的 [3] 树枝烯开始,通过中等稳定的例子,最后通过连续亚甲基化(使用二甲基锍甲基化)合成高度功能化、稳定的 [3] 树枝烯和 Horner-Wadsworth-Emmons 烯化。它还描述了影响其稳定性和与各种亲二烯体反应性的属性的研究。此外,它还报告了这些树枝状烯如何在巧妙的操纵下参与二烯传递的 Diels-Alder (DTDA) 序列,从而通过构建一个小而多样的复杂框架库来利用它们的全部潜力,以快速和高效的方式,具有步骤和原子经济。1 介绍 2 [3] 树枝烯合成的文献方法 3 我们与 [3] 树枝烯的幽会 3.1 与 Corey-Chaykovsky Ylide 的偶然烯烃化 3.2 [3] 树枝烯的合成和反应性/稳定性研究 3.3 [3] 树枝烯的 Diels-Alder 反应3.4 为 DTDA 反应调整 [3] 树枝烯 3.5 以多样性为导向的合成 [3] 树枝烯 3。
更新日期:2017-12-11
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