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Synthesis 2022; 54(10): 2415-2422
DOI: 10.1055/a-1730-8628
paper

Total Synthesis of Cryptopleurine and Its Analogues

Yousuke Yamaoka  ∗
,
Takuro Yamakawa
,
Kaito Tateishi
,
Kiyosei Takasu∗
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.
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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 agents

Supporting 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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