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

Congcong Han; Yang Chen; Yin Cheung Ching; Chi Sing Lee; Shuzhong He

doi:10.1039/d0qo00554a

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

Congcong Han, Yang Chen, Yin Cheung Ching, Chi Sing Lee, Shuzhong He^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2243-2246
Number of pages	4
Journal	Organic Chemistry Frontiers
Volume	7
Issue number	16
Early online date	8 Jul 2020
DOIs	https://doi.org/10.1039/d0qo00554a
Publication status	Published - 21 Aug 2020

Scopus Subject Areas

Organic Chemistry

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title = "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.",

author = "Congcong Han and Yang Chen and Ching, {Yin Cheung} and Lee, {Chi Sing} and Shuzhong He",

note = "Funding Information: We thank the National Natural Science Foundation of China (Grant No. 21861010, 21562011, and 21871017), the Guizhou Provincial Natural Science Foundation (Qian Ke He platform talents [2018]5781), the Case Base Construction Project for Guizhou Graduate Education (KCALK2017012), Guizhou University (No. [2017]32, [2014]36) and Baptist University of Hong Kong (RC-SGT2/18-19/SCI/005 and RC-ICRS-18-19-01A) for their financial support.",

year = "2020",

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doi = "10.1039/d0qo00554a",

language = "English",

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journal = "Organic Chemistry Frontiers",

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AU - Han, Congcong

AU - Chen, Yang

AU - Ching, Yin Cheung

AU - Lee, Chi Sing

AU - He, Shuzhong

N1 - Funding Information: We thank the National Natural Science Foundation of China (Grant No. 21861010, 21562011, and 21871017), the Guizhou Provincial Natural Science Foundation (Qian Ke He platform talents [2018]5781), the Case Base Construction Project for Guizhou Graduate Education (KCALK2017012), Guizhou University (No. [2017]32, [2014]36) and Baptist University of Hong Kong (RC-SGT2/18-19/SCI/005 and RC-ICRS-18-19-01A) for their financial support.

PY - 2020/8/21

Y1 - 2020/8/21

N2 - 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.

AB - 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.

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DO - 10.1039/d0qo00554a

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JF - Organic Chemistry Frontiers

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

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