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

Chea, JongMyong; Clive, Derrick L. J.

doi:doi:10.7939/r3-tp8t-r079

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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
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.

Language
- English
Citation for previous publication
- Chea, J., & Clive, D. L. J. (2015). Synthesis of (+)-Ipalbidine Based on 6-exo-trig Radical Cyclization of a β-Amino Radical. Journal of Organic Chemistry, 80(20), 10294–10298. https://doi-org.login.ezproxy.library.ualberta.ca/10.1021/acs.joc.5b01890