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Radical-mediated hydroalkylation of 2-vinylpyrrolidine derivatives: a versatile entry into indolizidine alkaloids

Abstract

A concise route for the preparation of two simple optically pure indolizidin-5-ones has been developed. The key chain elongation process was achieved using a triethylborane/catechol mediated hydroalkylation of Boc-protected 2-vinylpyrrolidines. By using complementary strategies, these two bicyclic lactams can be alkylated with complete control of the stereochemistry at C(5) and their conversion to a variety of indolizidine alkaloids such as coniceine, indolizidine 209D and 167B, 5-epi-indolizidine 249A and monomorine has been reported in the literature.

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Acknowledgements

This work was supported by the Swiss National Science Foundation (200020_172621) and the University of Bern. Sankar Rao Suravarapu was supported by the State Secretariat for Education, Research and Innovation (SERI) via a Swiss Government Excellence Scholarships for Foreign Scholars and Artists.

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Correspondence to Philippe Renaud.

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Conflict of interest The authors declare that they have no conflict of interest.

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Suravarapu, S.R., Peter, B. & Renaud, P. Radical-mediated hydroalkylation of 2-vinylpyrrolidine derivatives: a versatile entry into indolizidine alkaloids. Sci. China Chem. 62, 1504–1506 (2019). https://doi.org/10.1007/s11426-019-9598-1

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Keywords

  • alkenes
  • carbohydrogenation
  • radical reaction
  • catechol
  • triethylborane
  • α-iodoesters
  • allylamine