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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

Olivier, WJ, Gardiner, MG ORCID: 0000-0001-6373-4253, Bissember, AC ORCID: 0000-0001-5515-2878 and Smith, JA ORCID: 0000-0001-6313-3298 2018 , 'Brønsted acid-mediated annulations of pyrroles featuring N-tethered α,β-unsaturated ketones and esters: total syntheses of (±)-tashiromine and (±)-indolizidine 209I' , Tetrahedron, vol. 74, no. 38 , pp. 5436-5441 , doi: 10.1016/j.tet.2018.04.067.

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Abstract

This 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.

Item Type: Article
Authors/Creators:Olivier, WJ and Gardiner, MG and Bissember, AC and Smith, JA
Keywords: pyrrole, brønsted acid, intramolecular Michael addition, total synthesis, indolizidine, tashiromine
Journal or Publication Title: Tetrahedron
Publisher: Pergamon-Elsevier Science Ltd
ISSN: 0040-4020
DOI / ID Number: 10.1016/j.tet.2018.04.067
Copyright Information:

© 2018 Published by Elsevier Ltd.

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