Citation: Feng Zhang, Yujie Niu, Dacheng Hong, Yilin Ye, Yuhui Hua, Shihao Ding, Yandong Zhang. Synthetic studies towards atkamine[J]. Chinese Chemical Letters, ;2021, 32(2): 668-671. doi: 10.1016/j.cclet.2020.06.008 shu

Synthetic studies towards atkamine

Department of Chemistry and Key Laboratory of Chemical Biology of Fujian Province, iChEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China

ydzhang@xmu.edu.cn

Received Date: 6 May 2020
Revised Date: 20 May 2020
Accepted Date: 5 June 2020
Available Online: 6 June 2020

Figures(6)

Atkamine is a complex marine pyrroloiminoquinone alkaloid that comprises a heptacyclic scaffold bearing five different heterocycles and four contiguous stereocenters, and therefore it is a highly challenging target for synthetic chemists. We herein reported a modular synthetic strategy toward this alkaloid, featuring a formal [5 + 2] annulation and an asymmetric Michael addition. The efficient synthesis of the long-chain aliphatic aldehyde and chiral amino acetal fragments have been achieved. A simplified tetracyclic intermediate bearing the core structure of atkamine has been successfully constructed through the formal [5 + 2] annulation.
- Atkamine,
- Total synthesis,
- Alkaloid,
- [5 + 2] annulation,
- Michael addition
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