Organo-cation catalyzed enantioselective α-hydroxylation of pyridinone-fused lactones: asymmetric synthesis of SN-38 and irinotecan.

Autor: Tian, Jin-Rui, Qiao, Yu-Hao, Zhuang, Qing-Bo, Fan, Rong, Li, Zhen, Zhang, Xiao-Ming, Zhang, Fu-Min, Tu, Yong-Qiang
Předmět:
Zdroj: Chemical Communications; 9/18/2024, Vol. 60 Issue 73, p9954-9957, 4p
Abstrakt: A catalytic asymmetric α-hydroxylation of pyridinone-fused lactones, containing the core structure of camptothecin, is described. Development of a novel spiropyrrolidine amide (SPA) derived triazolium bromide organo-cation catalyst is crucial for a highly enantioselective oxidation, which also accommodates a wide array of lactones with various substituents. The resulting tricyclic tertiary alcohol with an oxa-quaternary carbon center can be further applied in the synthesis of SN-38 and irinotecan, two anti-cancer drugs derived from camptothecin. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index