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N-tosyl-1,2,3-triazoles as scaffolds for morpholines: the total synthesis of ()-chelonin A


Gunawan, N and Nutt, MJ and Bissember, AC and Smith, JA and Stewart, SG, N-tosyl-1,2,3-triazoles as scaffolds for morpholines: the total synthesis of (-)-chelonin A, Synlett, 34 pp. 1-5. ISSN 0936-5214 (2022) [Refereed Article]

Copyright Statement

2022. Thieme. All rights reserved.

DOI: doi:10.1055/a-1982-5433


Substituted morpholine derivatives appear frequently in biologically active compounds and thus novel routes towards such structures are of great synthetic interest. Herein, we report the total syntheses of chelonin A, a morpholine-derived marine natural product with reported antibacterial and anti-inflammatory activity. The key step in this process was a rhodium carbenoid 1,3-insertion into a bromohydrin OH bond, followed by annulation, leading to a 2,6-disubstituted-3,4-dihydro-2H-1,4-oxazine core. This work was then extended to deliver the first asymmetric total synthesis of ()-chelonin A using an enantioenriched bromohydrin, prepared in turn via asymmetric transfer hydrogenation of an α-bromoketone.

Item Details

Item Type:Refereed Article
Keywords:chelonin A, morpholine, total synthesis, rhodium catalysis
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:Gunawan, N (Miss Nina Gunawan)
UTAS Author:Bissember, AC (Associate Professor Alex Bissember)
UTAS Author:Smith, JA (Professor Jason Smith)
ID Code:155238
Year Published:2022
Funding Support:Australian Research Council (FT200100049)
Deposited By:Chemistry
Deposited On:2023-02-07
Last Modified:2023-03-20

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