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  • Title: An enantioselective strategy for the synthesis of (S)-tylophorine via one-pot intramolecular Schmidt/Bischler-Napieralski/imine-reduction cascade sequence.
    Author: Su B, Chen F, Wang Q.
    Journal: J Org Chem; 2013 Mar 15; 78(6):2775-9. PubMed ID: 23373672.
    Abstract:
    A novel enantioselective strategy for the total synthesis of (S)-tylophorine was developed in an overall yield of 48% with more than 99% ee from readily avaliable azido acid and phenanthryl alcohol. This route features an Evans stereoselective alkylation and an unprecedented one-pot intramolecular Schmidt/Bischler-Napieralski/imine-reduction cascade sequence, in which three new bonds and two rings formed in 84% yield. The intramolecular Schmidt rearrangement of the azido aldehyde was proved to be racemization-free.
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