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Effective asymmetric synthesis of the key chiral building blocks of 20(S)- and 20(R)-camptothecins

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Abstract

An effective diastereoselective synthesis of (S)-N,N-diethyl-2-formyl-2-(methoxymethoxy)butanamide and (S)-2-formyl-2-(methoxymethoxy)butanoic acid ethyl ester, which are two key chiral building blocks for the synthesis of 20(S)-camptothecins, has been developed by employing an asymmetric bromolactonization using (R)-proline. The (R) compounds were also synthesized to obtain 20(R)-camptothecin.

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Acknowledgments

We gratefully acknowledge the Shanghai Municipal Natural Science Foundation (10ZR1409600). We also thank the Laboratory of Organic Functional Molecules, the Sino-French Institute of ECNU for the support.

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Authors and Affiliations

  1. Department of Chemistry, East China Normal University, Shanghai, 200062, China

    Sanbao Yu, Xiangjun Feng, Yu Luo & Wei Lu

  2. Institute of Drug Discovery and Development, East China Normal University, Shanghai, 200062, China

    Wei Lu

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  1. Sanbao Yu
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  2. Xiangjun Feng
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  3. Yu Luo
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  4. Wei Lu
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Correspondence to Yu Luo or Wei Lu.

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Yu, S., Feng, X., Luo, Y. et al. Effective asymmetric synthesis of the key chiral building blocks of 20(S)- and 20(R)-camptothecins. Monatsh Chem 143, 675–681 (2012). https://doi.org/10.1007/s00706-011-0617-0

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  • DOI: https://doi.org/10.1007/s00706-011-0617-0

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