Issue 16, 2020
From the journal:

Organic Chemistry Frontiers

An approach towards the construction of the tetracyclic skeleton of palhinine alkaloids†

Congcong Han,a   Yang Chen,b   Yin-Cheung Ching,c   Chi-Sing Lee ORCID logo c  and  Shuzhong He ORCID logo *a  

* Corresponding authors

a School of Pharmaceutical Sciences, and Guizhou Engineering Laboratory for Synthetic Drugs, Guizhou University, Guiyang, Guizhou 550025, China
E-mail: szhe@gzu.edu.cn

b State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China

c Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong SAR

Abstract

A concise synthesis of the tetracyclic skeleton of palhinine alkaloids is described. The approach features a bifunctional Lewis acid promoted Diels–Alder/carbocyclization cascade for the rapid construction of the isotwistane (tricyclo[4.3.1.03,7]decane) core. This key reaction is highly diastereoselective and could be carried out on gram scale. The cyclization product already possesses the completed ring system of palhinine alkaloids and could potentially be further functionalized to palhinine A.

Graphical abstract: An approach towards the construction of the tetracyclic skeleton of palhinine alkaloids

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Article information

DOI
https://doi.org/10.1039/D0QO00554A
Article type
Research Article
Submitted
08 May 2020
Accepted
07 Jul 2020
First published
08 Jul 2020

Org. Chem. Front., 2020,7, 2243-2246

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An approach towards the construction of the tetracyclic skeleton of palhinine alkaloids

C. Han, Y. Chen, Y. Ching, C. Lee and S. He, Org. Chem. Front., 2020, 7, 2243 DOI: 10.1039/D0QO00554A

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