Divergent Syntheses of Pyridoacridine Alkaloids via Palladium‐Catalyzed Reductive Cyclization with Nitro‐Biarenes. Issue 7 (30th May 2021)

• Record Type: Journal Article
• Authors: Liu, Bo; Wang, Shuping; Bian, Changhao; Liao, Hongze; Lin, Hou‐Wen
• Is Part Of: Chinese journal of chemistry. Volume 39:Issue 7(2021)
• Page Start: 1905
• Page End: 1910
• Publication Date: 2021-05-30
• Subjects: Polycyclic heteroaromatics -- Palladium‐catalyzed reductive cyclization -- Marine nature alkaloids -- Divergent syntheses -- Pyridoacridine; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202100094
• Languages: English
• ISSNs: 1001-604X

Abstract

Main observation and conclusion: A divergent and novel protocol for the preparation of both pyrido[2, 3, 4‐ kl ]acridine and pyrido[4, 3, 2‐ kl ]acridine alkaloids was developed. This method featured the remote palladium‐catalyzed reductive cyclization with Mo(CO)6 as reductant. A wide range of substrates including three types of nitro arenes were tolerated and afforded corresponding products in good to excellent yields. This method has been successfully applied to the total synthesis of norsegoline, styelsamine C and the skeleton of necatorone. Abstract : A divergent and efficient method for preparing pyrido[2, 3, 4‐ kl ]acridine and pyrido[4, 3, 2‐ kl ]acridine alkaloid is reported. This method featured a novel remote palladium‐catalyzed reductive cyclization with Mo(CO)6 as reductant by nitro biarenes, and a wide scope of substrates were tolerated and total 34 analogues containing the two types of polycyclic heteroaromatic skeleton were prepared. Furthermore, the potential synthetic application of this method was demonstrated by the accomplishment of synthesis of norsegoline, styelsamine C and the necatorone skeleton.