Citation: Jindian Duan, Xiaojuan Ding, Pui Ying Choy, Binyan Xu, Luchao Li, Hong Qin, Zheng Fang, Fuk Yee Kwong, Kai Guo. Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway[J]. Chinese Chemical Letters, ;2024, 35(10): 109565. doi: 10.1016/j.cclet.2024.109565 shu

Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway

Jindian Duan ^a ,
Xiaojuan Ding ^a ,
Pui Ying Choy ^b ,
Binyan Xu ^a ,
Luchao Li ^a ,
Hong Qin ^a ,
Zheng Fang ^a ,
Fuk Yee Kwong ^{b, *,} ,
Kai Guo ^{a, *,}

a.
College of Biotechnology and Pharmaceutical Engineering, State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing 211816, China
b.
Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Hong Kong, China

fykwong@cuhk.edu.hk

guok@njtech.edu.cn

Received Date: 5 September 2023
Revised Date: 18 January 2024
Accepted Date: 28 January 2024
Available Online: 1 February 2024

Figures(5)

An oxidative annulation of 2-arylidene-1,3-indanediones with Meldrum's acid has been developed for the divergent syntheses of spirolactones with a spirocenter located at the γ-position with respect to the carbonyl group. This heteroannulation protocol tolerates various functional groups and delivers moderate-to-good product yields. Interestingly, the reaction outcomes are exclusively controlled by the reaction oxidant/medium. This annulation strategy can also be executed in the flow system with decent product yields. Control experiments revealed that the reaction proceeds via a radical tandem annulation pathway.
- Spirolactonisation,
- γ-Spirolactones,
- 2-Arylidene-1,3-indanediones,
- Meldrum's acid,
- Divergent synthesis
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