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

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journal contribution
posted on 16.10.2015 by JongMyoung Chea, Derrick L. J. Clive
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%.

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