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

Abstract
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-trig radical cyclization (Bu3SnH, AIBN, PhMe, 110 °C), dehydration (P2O5, H3PO4), and demethylation (BBr3) gave (+)-ipalbidine with ee >99%.
AuthorsJongMyoung Chea, Derrick L J Clive
JournalThe Journal of organic chemistry (J Org Chem) Vol. 80 Issue 20 Pg. 10294-8 (Oct 16 2015) ISSN: 1520-6904 [Electronic] United States
PMID26402510 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • 2-((phenylselanyl)methyl)pyrrolidine
  • 2-bromo-1-(4-methoxyphenyl)ethan-1-one
  • Amines
  • Free Radicals
  • Indolizines
  • Organoselenium Compounds
  • Pyrrolidines
  • ipalbidine
  • Proline
  • Ethane
Topics
  • Alkylation
  • Amines (chemistry)
  • Cyclization
  • Ethane (analogs & derivatives, chemistry)
  • Free Radicals (chemistry)
  • Indolizines (chemical synthesis, chemistry)
  • Molecular Structure
  • Organoselenium Compounds
  • Proline (chemistry)
  • Pyrrolidines (chemical synthesis, chemistry)
  • Stereoisomerism

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