Palladium-catalyzed post-Ugi arylative dearomatization/Michael addition cascade towards plicamine analogues

Chao Liu; Ruiqi Zhao; Liangliang Song; Zhenghua Li; Guilong Tian; Yi He; Luc Van Meervelt; Vsevolod A. Peshkov; Erik V. Van der Eycken

doi:10.1039/D1OB01805A

Palladium-catalyzed post-Ugi arylative dearomatization/Michael addition cascade towards plicamine analogues†

Chao Liu,‡^a Ruiqi Zhao,‡^a Liangliang Song,*^b Zhenghua Li,

^a Guilong Tian,

^a Yi He,^a Luc Van Meervelt,^c Vsevolod A. Peshkov^de and Erik V. Van der Eycken

*^af

Author affiliations

* Corresponding authors

^a Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven Celestijnenlaan 200F, Leuven, Belgium
E-mail: erik.vandereycken@kuleuven.be

^b Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu, China
E-mail: liangliangsong@njfu.edu.cn

^c Biomolecular Architecture, Department of Chemistry, KU Leuven Celestijnenlaan 200F, Leuven, Belgium

^d College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou 215123, China

^e Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Ave, Nur-Sultan 010000, Republic of Kazakhstan

^f Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow, Russia

Abstract

A palladium-catalyzed intramolecular cyclization of Ugi-adducts via a cascade dearomatization/aza-Michael addition process has been developed. Diverse plicamine analogues are constructed in a rapid, highly efficient and step-economical manner, through the combination of an Ugi-4CR and a palladium-catalyzed dearomatization. The synthetic utility of this approach is illustrated by further functional group transformations.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D1OB01805A
Article type: Paper
Submitted: 14 Sep 2021
Accepted: 28 Oct 2021
First published: 28 Oct 2021

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Org. Biomol. Chem., 2021,19, 9752-9757

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Palladium-catalyzed post-Ugi arylative dearomatization/Michael addition cascade towards plicamine analogues

C. Liu, R. Zhao, L. Song, Z. Li, G. Tian, Y. He, L. Van Meervelt, V. A. Peshkov and E. V. Van der Eycken, Org. Biomol. Chem., 2021, 19, 9752 DOI: 10.1039/D1OB01805A

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Organic & Biomolecular Chemistry

Palladium-catalyzed post-Ugi arylative dearomatization/Michael addition cascade towards plicamine analogues†

Abstract

Supplementary files

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Palladium-catalyzed post-Ugi arylative dearomatization/Michael addition cascade towards plicamine analogues

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