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

Org Biomol Chem. 2021 Nov 18;19(44):9752-9757. doi: 10.1039/d1ob01805a.

Authors

Chao Liu¹, Ruiqi Zhao¹, Liangliang Song², Zhenghua Li¹, Guilong Tian¹, Yi He¹, Luc Van Meervelt³, Vsevolod A Peshkov^{4

5}, Erik V Van der Eycken^{1

6}

Affiliations

¹ Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven Celestijnenlaan 200F, 3001, Leuven, Belgium. erik.vandereycken@kuleuven.be.
² 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. liangliangsong@njfu.edu.cn.
³ Biomolecular Architecture, Department of Chemistry, KU Leuven Celestijnenlaan 200F, 3001, Leuven, Belgium.
⁴ College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou 215123, China.
⁵ Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Ave, Nur-Sultan 010000, Republic of Kazakhstan.
⁶ Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow, 117198, Russia.

PMID: 34730164
DOI: 10.1039/d1ob01805a

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.

Publication types

Research Support, Non-U.S. Gov't