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Synthesis 2011(24): 4045-4049  
DOI: 10.1055/s-0031-1289575
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel and Enantioselective Total Synthesis of (20S)-Camptothecin via a Sharpless Asymmetric Dihydroxylation Strategy

Lei Zhaoa,b, Fang-Jun Xionga, Wen-Xue Chena, Fen-Er Chen*a,b
a Fudan-DSM Joint Lab for Synthetic Method and Chiral Technology, Department of Chemistry, Fudan University, Shanghai, 200433, P. R. of China
b Institutes of Biomedical Sciences, Fudan University, Shanghai, 200031, P. R. of China
Fax: +86(21)65643811; e-Mail: rfchen@fudan.edu.cn;
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Publication History

Received 6 September 2011
Publication Date:
25 October 2011 (online)

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Abstract

A novel and efficient asymmetric total synthesis of (20S)-camptothecin has been accomplished in an overall yield of 12% starting from the commercially available 2-methoxynicotinic acid. The key step in the sequence is the Sharpless asymmetric dihydroxylation of a 4-(but-1-en-2-yl)pyridine derivative to establish the stereocenter of (20S)-camptothecin.

Key words

total synthesis - stereoselectivity - asymmetric catalysis - antitumor agents - Heck reaction

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