Biomimetic Total Syntheses of Ergot Alkaloids via Decarboxylative Giese Coupling

Biomimetic Total Syntheses of Ergot Alkaloids via Decarboxylative Giese Coupling

Biomimetic total syntheses of Festuclavine and Pyroclavine were achieved by a sequential radical coupling. The key steps include intramolecular decarboxylative Giese reaction to form the central C ring and 4-nitrobenzenesulfonyl (Ns)-directed indole C4–H olefination to introduce the indole C4 compon...

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Veröffentlicht in:Organic letters 2021-01, Vol.23 (2), p.370-375
Hauptverfasser: Ge, Yuhua, Wang, Hang, Wang, Hua-Nan, Yu, Shu-Sheng, Yang, Rui, Chen, Xingyue, Zhao, Qin, Chen, Gang
Format: Artikel
Sprache:eng
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Zusammenfassung:Biomimetic total syntheses of Festuclavine and Pyroclavine were achieved by a sequential radical coupling. The key steps include intramolecular decarboxylative Giese reaction to form the central C ring and 4-nitrobenzenesulfonyl (Ns)-directed indole C4–H olefination to introduce the indole C4 component. In addition, D-ring formation was completed by decarboxylative alkenylation and intramolecular SN2 reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03867