First total synthesis of type II abyssomicins: (±)-abyssomicin 2 and (±)-neoabyssomicin B
First total synthesis of type II abyssomicins: (±)-abyssomicin 2 and (±)-neoabyssomicin B
The intramolecular Diels-Alder reaction (IMDA) of a butenolide derivative, as an entry to the type II abyssomicin scaffold, and the total synthesis of (±)-abyssomicin 2 and (±)-neoabyssomicin B are reported for the first time. A facile route to the IMDA precursor, the formation of a type I intermediate and two paths to (±)-neoabyssomicin B are also discussed.
3761-3765
Canko, Aleksander
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Athanassopoulou, Georgia D.
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Psycharis, Vassilis
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Raptopoulou, Catherine P.
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Herniman, Julie M.
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Mouchtouris, Vasileios
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Foscolos, Angeliki Sofia
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Couladouros, Elias A.
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Vidali, Veroniki P.
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10 May 2023
Canko, Aleksander
efcf7fa9-3b01-430f-9469-b7d97b68492a
Athanassopoulou, Georgia D.
71522def-bf68-40bd-9c84-5907bfe6fc0f
Psycharis, Vassilis
fad102df-b322-4aa0-aaa8-2aeb847141e6
Raptopoulou, Catherine P.
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Herniman, Julie M.
530b1a36-1386-4602-8df7-defa6eb3512b
Mouchtouris, Vasileios
6bcfb509-f57c-4836-addb-810e4dabd67e
Foscolos, Angeliki Sofia
94dbaf7d-057e-4d54-a9e5-2b503b1dc10e
Couladouros, Elias A.
8d090bee-1ec2-43ef-8c3a-0a06e62a7293
Vidali, Veroniki P.
b2e1bca5-8746-4827-a5af-6e4f95543a24
Canko, Aleksander, Athanassopoulou, Georgia D., Psycharis, Vassilis, Raptopoulou, Catherine P., Herniman, Julie M., Mouchtouris, Vasileios, Foscolos, Angeliki Sofia, Couladouros, Elias A. and Vidali, Veroniki P.
(2023)
First total synthesis of type II abyssomicins: (±)-abyssomicin 2 and (±)-neoabyssomicin B.
Organic and Biomolecular Chemistry, 21 (18), .
(doi:10.1039/d3ob00476g).
Abstract
The intramolecular Diels-Alder reaction (IMDA) of a butenolide derivative, as an entry to the type II abyssomicin scaffold, and the total synthesis of (±)-abyssomicin 2 and (±)-neoabyssomicin B are reported for the first time. A facile route to the IMDA precursor, the formation of a type I intermediate and two paths to (±)-neoabyssomicin B are also discussed.
Text
d3ob00476g
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More information
Accepted/In Press date: 17 April 2023
e-pub ahead of print date: 18 April 2023
Published date: 10 May 2023
Additional Information:
Funding Information:
This research is co-financed by Greece and the European Union (European Social Fund- ESF) through the Operational Programme “Human Resources Development, Education and Lifelong Learning” in the context of the project “Strengthening Human Resources Research Potential via Doctorate Research – 2 Cycle” (MIS-5000432), implemented by the State Scholarships Foundation (IKY). nd
Identifiers
Local EPrints ID: 477193
URI: http://eprints.soton.ac.uk/id/eprint/477193
ISSN: 1477-0520
PURE UUID: 4af78669-8f22-4322-87b5-4bda5cf22489
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Date deposited: 01 Jun 2023 16:31
Last modified: 18 Mar 2024 02:50
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Contributors
Author:
Aleksander Canko
Author:
Georgia D. Athanassopoulou
Author:
Vassilis Psycharis
Author:
Catherine P. Raptopoulou
Author:
Vasileios Mouchtouris
Author:
Angeliki Sofia Foscolos
Author:
Elias A. Couladouros
Author:
Veroniki P. Vidali
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