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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

Citation

Olivier, WJ and Gardiner, MG and Bissember, AC and Smith, JA, Brønsted acid-mediated annulations of pyrroles featuring N-tethered α,β-unsaturated ketones and esters: total syntheses of (±)-tashiromine and (±)-indolizidine 209I, Tetrahedron, 74, (38) pp. 5436-5441. ISSN 0040-4020 (2018) [Refereed Article]

Copyright Statement

© 2018 Published by Elsevier Ltd.

DOI: doi:10.1016/j.tet.2018.04.067

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 Details

Item Type:Refereed Article
Keywords:pyrrole, brønsted acid, intramolecular Michael addition, total synthesis, indolizidine, tashiromine
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
UTAS Author:Olivier, WJ (Mr Wesley Olivier)
UTAS Author:Gardiner, MG (Associate Professor Michael Gardiner)
UTAS Author:Bissember, AC (Dr Alex Bissember)
UTAS Author:Smith, JA (Associate Professor Jason Smith)
ID Code:128084
Year Published:2018
Web of Science® Times Cited:1
Deposited By:Chemistry
Deposited On:2018-09-01
Last Modified:2019-03-07
Downloads:0

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