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Exploring cyclization strategies to access stemona alkaloids: subtle effects influencing reactivity in intramolecular Michael additions
Citation
Olivier, WJ and Babaahmadi, R and Lucas, N and Ariafard, A and Bissember, AC and Smith, JA, Exploring cyclization strategies to access stemona alkaloids: subtle effects influencing reactivity in intramolecular Michael additions, Organic Letters, 23, (21) pp. 8494-8498. ISSN 1523-7060 (2021) [Refereed Article]
Copyright Statement
Copyright 2021 American Chemical Society
DOI: doi:10.1021/acs.orglett.1c03205
Abstract
This report investigates the fundamental basis for rather surprising patterns of reactivity in Brønsted acid-mediated cyclizations of pyrrole substrates bearing pendant Michael acceptors that were identified during syntheses of Stemona alkaloids. Integrated experimental and theoretical studies reveal the profound influence that substituent effects have on the viability of these transformations. Additionally, we identify that electronic effects, in addition to barrier-lowering secondary orbital interactions within transition states, account for the exclusive preference for 7-endo-trig cyclizations over 6-exo-trig cyclizations.
Item Details
Item Type: | Refereed Article |
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Keywords: | stemona alkaloids, pyrrole, Michael addition, DFT |
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: | Babaahmadi, R (Mr Rasool Babaahmadi) |
UTAS Author: | Ariafard, A (Associate Professor Alireza Ariafard) |
UTAS Author: | Bissember, AC (Associate Professor Alex Bissember) |
UTAS Author: | Smith, JA (Professor Jason Smith) |
ID Code: | 147736 |
Year Published: | 2021 |
Funding Support: | Australian Research Council (FT200100049) |
Web of Science® Times Cited: | 5 |
Deposited By: | Chemistry |
Deposited On: | 2021-11-12 |
Last Modified: | 2022-08-19 |
Downloads: | 0 |
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