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Synthesis 2019; 51(18): 3506-3510
DOI: 10.1055/s-0037-1611870
paper
© Georg Thieme Verlag Stuttgart · New York

A Concise Total Synthesis of (±)-Camptothecin

Qian Liu
a   Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, P. R. of China   Email: rfchen@fudan.edu.cn
b   Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Molecules, Shanghai 200433, P. R. of China
,
Guan-xin Huang
a   Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, P. R. of China   Email: rfchen@fudan.edu.cn
b   Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Molecules, Shanghai 200433, P. R. of China
,
Min-jie Liu
a   Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, P. R. of China   Email: rfchen@fudan.edu.cn
b   Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Molecules, Shanghai 200433, P. R. of China
,
Fen-Er Chen∗
a   Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, P. R. of China   Email: rfchen@fudan.edu.cn
b   Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Molecules, Shanghai 200433, P. R. of China
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Publication History

Received: 16 April 2019

Accepted after revision: 31 May 2019

Publication Date:
26 June 2019 (online)

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A Concise Total Synthesis of (±)-CamptothecinSynthesis 2019; 51(18): e3-e3
DOI: 10.1055/s-0039-1690023

Abstract

A total synthesis of racemic camptothecin, characterized by a concise construction of the ring systems and easy functional group transformation, is described. A domino reaction consisting of a Heck reaction and an aza-intramolecular Michael addition to form the C ring serves as the first key step in the synthesis. The D ring was constructed by a simple Wittig–Horner reaction followed by removal of the protective groups. Hydroxymethylation, demethylation, and lactone formation reactions were performed in one-pot to construct the E ring under hydrobromic acid conditions. This work provides an efficient scheme for further synthetic exploration of camptothecin and its analogues.

Key words

camptothecin - total synthesis - domino reaction - Heck reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611870.
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