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Enantiopure Pyrroline-N-Oxides for the Synthesis of Pyrrolizine and Indolizine Alkaloids

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Current Trends in Organic Synthesis

Abstract

The total synthesis of natural products requires new and selective methods to address the structural complexity that the nature is able to introduce in natural compounds. This is the challenge that gives the impetus to organic chemists to find new reactions, new reagents and new catalysts to run reactions in a chemoselective, regioselective and stereoselective way. Recently, the horizon has moved to explore the development of new synthetic strategies, like domino or multicomponent,1 combinatorial2 or enzymatic3 processes, that have expanded the synthetic tools available to researchers. On the other hand, the concern of chemists has shifted to modern topics like atom economy4 and environmentally friendly syntheses. In the light of all these points we approached the synthesis of natural products belonging to the classes of indolizine5 and pyrrolizine6 alkaloids which are attracting growing interest from synthetic chemists for their various and essential biological activities. Among these are glycosidase inhibitors (with indolizidine or pyrrolizidine skeletons) 7 and necine bases (with pyrrolizidine skeletons)6 (Chart 1).

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Brandi, A., Cardona, F., Cicchi, S., Cordero, F.M., Goti, A. (1999). Enantiopure Pyrroline-N-Oxides for the Synthesis of Pyrrolizine and Indolizine Alkaloids. In: Scolastico, C., Nicotra, F. (eds) Current Trends in Organic Synthesis. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4801-0_27

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  • DOI: https://doi.org/10.1007/978-1-4615-4801-0_27

  • Publisher Name: Springer, Boston, MA

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