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Brønsted acid-mediated annulations of pyrroles featuring N-tethered α,β-unsaturated ketones and esters: total syntheses of (±)-tashiromine and (±)-indolizidine 209I
journal contribution
posted on 2023-05-19, 20:55 authored by Wesley Olivier, Michael GardinerMichael Gardiner, Alexander BissemberAlexander Bissember, Jason SmithJason SmithThis study provides the first report of the construction of tetrahydroindolizines and tetrahydropyrrolo [1,2-a]azepines via Brønsted acid-mediated annulation of pyrroles featuring N-tethered α,β-unsaturated esters. In addition, the Brønsted acid-catalyzed cyclization of pyrroles featuring pendant α,β-unsaturated ketones was applied to complete total syntheses of the indolizidine alkaloids (±)-tashiromine and (±)-indolizidine 209I.
History
Publication title
TetrahedronVolume
74Issue
38Pagination
5436-5441ISSN
0040-4020Department/School
School of Natural SciencesPublisher
Pergamon-Elsevier Science LtdPlace of publication
The Boulevard, Langford Lane, Kidlington, Oxford, England, Ox5 1GbRights statement
© 2018 Published by Elsevier Ltd.Repository Status
- Restricted