カンプトテシンの生合成に触発された不斉全合成
Shan-Shan Li1, Xiao-Guang Wu1, Zhen Li1
1State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China. tuyq@lzu.edu.cn.
Abstract:
An asymmetric total synthesis of camptothecin taking advantage of a biosynthetic skeletal transformation is described. The synthesis features an improved one-pot Mannich/acylation/Wittig reaction enabled by a newly developed N-sulfonylated amide catalyst, intramolecular [4+2] cycloaddition, a highly diastereoselective dihydroxylation, and a late-stage scaffold transformation from a monoterpene indole to give a quinoline framework via a Winterfeldt oxidation. These key steps collectively enable a concise and enantioselective synthesis of the antitumor agent (20S)-camptothecin.
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