Citation: Yang Xiaohui, Gu Xuesong, Bin Huaiyu, Xie Jianhua, Zhou Qilin. Asymmetric Synthesis of (-)-Indolizidine167B and (+)-Coniine[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3963-3968. doi: 10.6023/cjoc202007052 shu

Asymmetric Synthesis of (-)-Indolizidine167B and (+)-Coniine

State Key Laboratory and Institute of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071

Corresponding author: Xie Jianhua, jhxie@nankai.edu.cn Zhou Qilin, qlzhou@nankai.edu.cn
Received Date: 22 July 2020
Revised Date: 29 July 2020
Available Online: 11 August 2020
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21532003, 21871152, 21790332)the National Natural Science Foundation of China 21532003the National Natural Science Foundation of China 21871152the National Natural Science Foundation of China 21790332

Figures(5)

The enantioselective syntheses of (-)-indolizidine 167B and (+)-coniine were described based on the asymmetric hydrogenation of racemic δ-hydroxy esters via kinetic resolution. With optically active chiral δ-hydroxy ester (S)-4 and chiral 1, 5-diol (R)-5 obtained by asymmetric hydrogenation of racemic ethyl 5-hydroxyoctanoate (rac-4) with chiral spiro iridium catalyst Ir-(R)-SpiroPAP as chiral starting materials, the efficient enantioselective syntheses of (-)-indolizidine 167B and (+)-coniine were achieved by using intramolecular reductive amination and N-substitution/cyclization, respectively, as a key step to construct the chiral aza-bicyclic[4.3.0]nonane skeleton and chiral piperidine ring. This provides new efficient methods for enantioselective syntheses of indolizidine and piperidine alkaloids.
- alkaloids,
- asymmetric hydrogenation,
- indolizidine,
- coniine,
- reductive amination
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