Synthesis of (+)-Ipalbidine Based on 6-exo-trig Radical Cyclization of a β-Amino Radical.
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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
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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%.
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http://purl.org/coar/resource_type/c_6501 http://purl.org/coar/version/c_b1a7d7d4d402bcce http://purl.org/coar/version/c_71e4c1898caa6e32
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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.
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en