Journal
TETRAHEDRON
Volume 74, Issue 38, Pages 5436-5441Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.04.067
Keywords
Pyrrole; Bronsted acid; Intramolecular Michael addition; Total synthesis; Indolizidine; Tashiromine
Categories
Funding
- School of Natural Sciences - Chemistry
- Australian Government
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This study provides the first report of the construction of tetrahydroindolizines and tetrahydropyrrolo [1,2-a]azepines via Bronsted acid-mediated annulation of pyrroles featuring N-tethered alpha,beta-unsaturated esters. In addition, the Bronsted acid-catalyzed cyclization of pyrroles featuring pendant alpha,beta-unsaturated ketones was applied to complete total syntheses of the indolizidine alkaloids (+/-)-tashiromine and (+/-)-indolizidine 209I. (C) 2018 Published by Elsevier Ltd.
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