Synthesis of Phenanthridine derivatives from Arynes and Ketimines via aza-Diels-Alder/decarboxylation reactions

The aza -Diels-Alder and decarboxylation reactions have been developed for the synthesis of a variety of functionalized phenanthridine . The approach by using ketimine and arynes constructed the phenanthridine core smoothly and efficiently. With this strategy, an expeditious total synthesis of the natural products trispheridine and nornitidine has been realized. • Polycyclic compound was constructed in one-step by using aryne as the key intermediate. • The natural products trispheridine and nornitidine could be constructed efficiently via the developed strategy. • Target product phenanthridines possess great potential to be transformed into derivatives with wide applications.

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Publication Details

Journal
Tetrahedron Letters
Published
2025-04-01
DOI
https://doi.org/10.1016/j.tetlet.2025.155557
Primary Topic
Cyclization and Aryne Chemistry
Type
article
Field-Weighted Citation Impact
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article

Synthesis of Phenanthridine derivatives from Arynes and Ketimines via aza-Diels-Alder/decarboxylation reactions

Feng Sha, Ruiyang Yu, Han Tao, Xinyan Wu et al.
2 links
Tetrahedron Letters
Cyclization and Aryne Chemistry
article

Synthesis of Phenanthridine derivatives from Arynes and Ketimines via aza-Diels-Alder/decarboxylation reactions

Feng Sha, Ruiyang Yu, Han Tao, Xinyan Wu, R. Tang, Manli Xu
article en

Abstract

The aza -Diels-Alder and decarboxylation reactions have been developed for the synthesis of a variety of functionalized phenanthridine . The approach by using ketimine and arynes constructed the phenanthridine core smoothly and efficiently. With this strategy, an expeditious total synthesis of the natural products trispheridine and nornitidine has been realized. • Polycyclic compound was constructed in one-step by using aryne as the key intermediate. • The natural products trispheridine and nornitidine could be constructed efficiently via the developed strategy. • Target product phenanthridines possess great potential to be transformed into derivatives with wide applications.

Tetrahedron LettersVol. 161
East China University of Science and Technology (CN)
Openalex Percentile: Top 95%
Cyclization and Aryne Chemistry
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