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Progress in Chemistry 2010, Vol. 22 Issue (01): 81-90 Previous Articles   Next Articles

• Invited Article •

Inspiration from Protecting-Group-Free Synthesis

Li Xuqin1;  Liu An2**   

  1. (1.School of Applied Science, University of Science and Technology Beijing, Beijing 100083, China; 2.Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China)
  • Received: Revised: Online: Published:
  • Contact: Liu An E-mail:liuan62@hotmail.com
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Inspired by protecting-group-free synthesis of ambiguine H, welwitindolinone A and other complex natural products, the review illustrates that protecting-group-free synthesis brings real advantages with regard to the number of operations in a synthetic sequence, and the accompanying decrease in loss of material. To avoid the use of protecting groups, for a natural product target, one can "go back to basic", and devise a biomimetic pathway. However, for non-natural products, efforts should be put more on the discovery of new reactivity and principles for controlling chemoselectivity. In addition, we should follow several guidelines: maximizing the percentage of C-C bond forming or breaking events relative to the total number of steps in a synthesis, introducing sensitive functional group after skeleton building reactions, and relying on highly chemoselective reactions such as transition-metal-catalyzed or free-radical reactions to build skeleton. Through listing further examples of protecting-group-free synthesis, the paper reveals that researchers should exploit innate reactivity of functional groups and make their efforts on the invention of new methodology to reduce the number of protecting groups.

Contents
1 Introduction
2 The way of "go back to basic"
3 Strategies of protecting-group-free synthesis
3.1 Reliance on transition-metal-catalyzed reactions
3.2 Introduction sensitive functional group in the end
3.3 Exploitation of innate reactivity of functional groups
4 Conclusion

Key words: protecting-group-free, chemoselectivity, go back to basic, biomimetic synthesis, transition-metal catalyzed

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