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Unified total syntheses of (±)-sessilifoliamides B, C, and D


Olivier, WJ and Bissember, AC and Smith, JA, Unified total syntheses of ( )-sessilifoliamides B, C, and D, Organic Letters, 23, (9) pp. 3437-3441. ISSN 1523-7060 (2021) [Refereed Article]

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Copyright 2021 American Chemical Society

DOI: doi:10.1021/acs.orglett.1c00895


The first total syntheses of the Stemona alkaloids sessilifoliamides B and D and the second synthesis of sessilifoliamide C have been completed from a simple pyrrole substrate. The bicyclic lactam core was prepared on a gram scale via a Brønsted acid mediated cyclization and controlled oxidation with Dess–Martin periodinane. This delivered sessilifoliamide C (and its C-11 epimer) in 24% yield over 11 steps, and sessilifoliamides B and D in 13 and 17 steps, respectively.

Item Details

Item Type:Refereed Article
Keywords:Stemona, sessilifoliamide, polycyclic alkaloids, lactam
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:144286
Year Published:2021
Web of Science® Times Cited:8
Deposited By:Chemistry
Deposited On:2021-05-07
Last Modified:2021-06-21

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