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Revised structures of dehydrostenines A and B: total syntheses of (±)-dehydrostenine A and structure assigned to dehydrostenine B

Citation

Olivier, WJ and Lucas, NT and Bissember, AC and Smith, JA, Revised structures of dehydrostenines A and B: total syntheses of (±)-dehydrostenine A and structure assigned to dehydrostenine B, Chemistry: A European Journal, 27 pp. 15382-15386. ISSN 0947-6539 (2021) [Refereed Article]


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DOI: doi:10.1002/chem.202102651

Abstract

The first total syntheses of the Stemona alkaloid dehydrostenine A and the structure assigned to dehydrostenine B have been completed from a simple pyrrole substrate in 10 and 11 steps, respectively. Two independent Brønsted-acid-mediated intramolecular Michael additions were exploited to construct the tetracyclic dehydrostenine core. As a result of synthetic studies and associated analysis of the relevant literature, revisions of the structures originally assigned to dehydrostenines A and B are proposed.

Item Details

Item Type:Refereed Article
Keywords:dehydrostenines, pyrrole, Stemona alkaloids, total synthesis
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:Bissember, AC (Associate Professor Alex Bissember)
UTAS Author:Smith, JA (Associate Professor Jason Smith)
ID Code:147533
Year Published:2021
Funding Support:Australian Research Council (FT200100049)
Web of Science® Times Cited:1
Deposited By:Chemistry
Deposited On:2021-11-06
Last Modified:2021-11-15
Downloads:0

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