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Synthesis 2022; 54(10): 2415-2422
DOI: 10.1055/a-1730-8628
DOI: 10.1055/a-1730-8628
paper
Total Synthesis of Cryptopleurine and Its Analogues
This work was financially supported by JSPS KAKENHI (Grants 18K05103 and 19H03350), MEXT KAKENHI (Grant JP21H05212) in Digi-TOS, and the AMED Platform for Supporting Drug Discovery and Life Science Research (Grant jp19am0101092j0003). Y.Y. thanks the Takeda Science Foundation for financial support.
![](https://www.thieme-connect.de/media/synthesis/202210/lookinside/thumbnails/ss-2021-f0721-op_10-1055_a-1730-8628-1.jpg)
Abstract
Total synthesis of phenanthroquinolizidine alkaloid cryptopleurine was achieved in 8 steps from commercially available 2-pyridinecarboxaldehyde and the epoxide derived from methyleugenol. The key intermediate vinyl triflate enables the divergent synthesis of cryptopleurine derivatives by late-stage installation of various substituents on the C-ring.
Key words
heterocycles - phenanthroquinolizidines - cryptopleurine - natural product synthesis - cyclization - anticancer agentsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1730-8628.
- Supporting Information
Publication History
Received: 29 November 2021
Accepted after revision: 04 January 2022
Accepted Manuscript online:
04 January 2022
Article published online:
21 February 2022
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For reviews of phenanthroindolizidine and phenanthroquinoizidine alkaloids, see:
Recent examples of total synthesis of cryptopleurine, see: