Issue 16, 2020

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
08 May 2020
Accepted
07 Jul 2020
First published
08 Jul 2020

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

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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