关于α-吡喃酮与萜烯醌通过简便的狄尔斯-阿尔德反应途径快速合成各种天然骨架的评估。

Assessment on facile Diels-Alder approach of α-pyrone and terpenoquinone for the expedient synthesis of various natural scaffolds.

作者信息

Rammohan Aluru, Khasanov Albert F, Kopchuk Dmitry S, Gunasekar Duvvuru, Zyryanov Grigory V, Chupakhin Oleg N

机构信息

Ural Federal University, 19 Mira St., Ekaterinburg, 620002, Russian Federation.

Natural Products Division, Department of Chemistry, Sri Venkateswara University, Tirupati, 517502, India.

出版信息

Nat Prod Bioprospect. 2022 Mar 31;12(1):12. doi: 10.1007/s13659-022-00333-4.

DOI:10.1007/s13659-022-00333-4

PMID:35357593

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8971220/

Abstract

The development of highly facile synthetic procedures for the expedient synthesis of complex natural molecules is always in demand. As this aspect, the Diels-Alder reaction (DAR) has a versatile approach to the synthesis of complex natural compounds and highly regio-/stereoselcetive heterocyclic scaffolds. Additionally, α-pyrone and terpenoquinone are two versatile key intermediates that are prevalent in various bioactive natural compounds for instance, (±)-crinine, (±)-joubertinamine, (±)-pancratistatin, (-)-cyclozonarone, and 8-ephipuupehedione, etc. Hence, the current review summarizes the Diels-Alder reaction application of α-pyrone and terpenoquinone to the constructive synthesis of various natural products over the past two decades (2001-2021). Equally, it serves as a stencil for the invention and development of new synthetic strategies for high-complex molecular structured natural and heterocyclic molecules.

摘要

一直以来都需要开发高度简便的合成方法来快速合成复杂的天然分子。在这方面，狄尔斯-阿尔德反应（DAR）是合成复杂天然化合物和高度区域/立体选择性杂环支架的一种通用方法。此外，α-吡喃酮和萜烯醌是两种通用的关键中间体，它们在各种生物活性天然化合物中普遍存在，例如（±）-环戊胺、（±）-茹贝他明、（±）- Pancratistatin、（-）-环 zonarone 和 8-表普乌佩赫二酮等。因此，本综述总结了过去二十年（2001-2021 年）α-吡喃酮和萜烯醌在狄尔斯-阿尔德反应中用于各种天然产物的构建合成中的应用。同样，它为高复杂分子结构的天然和杂环分子的新合成策略的发明和开发提供了一个模板。