Synthesis of (+)-Ipalbidine Based on 6-exo-trig Radical Cyclization of a β-Amino Radical.

• Author(s) / Creator(s)

  • Chea, JongMyong
  • Clive, Derrick L. J.

• N-Boc (S)-proline was converted into (2S)-2-[(phenylselanyl)methyl]pyrrolidine which was
  alkylated on nitrogen with 2-bromo-1-(4-methoxyphenyl)ethan-1-one. Reaction with
  vinyllithium, 6-exo-trigonal radical cyclization (Bu3SnH, AIBN, PhMe, 110 °C), dehydration
  (P2O5, H3PO4) and demethylation (BBr3) gave (+)-ipalbidine with ee >99%.

• Date created

  2015-01-01

• Subjects / Keywords

  • Alkylation
  • Amines
  • Cyclization
  • Ethane
  • Free Radicals
  • Indolizines
  • Molecular Structure
  • Proline
  • Pyrrolidines
  • Steroisomerism
  • Ipalbidine

• Type of Item

  Article (Draft / Submitted)

• DOI

  https://doi.org/10.7939/r3-tp8t-r079

• License

  This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © 2015 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.5b01890.