Issue 73, 2024

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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
23 7 2024
Accepted
09 8 2024
First published
12 8 2024

Chem. Commun., 2024,60, 9954-9957

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

J. Tian, Y. Qiao, Q. Zhuang, R. Fan, Z. Li, X. Zhang, F. Zhang and Y. Tu, Chem. Commun., 2024, 60, 9954 DOI: 10.1039/D4CC03580A

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