First total synthesis of type II abyssomicins: (±)-abyssomicin 2 and (±)-neoabyssomicin B

Aleksander Canko; Georgia D. Athanassopoulou; Vassilis Psycharis; Catherine P. Raptopoulou; Julie M. Herniman; Vasileios Mouchtouris; Angeliki Sofia Foscolos; Elias A. Couladouros; Veroniki P. Vidali

doi:10.1039/D3OB00476G

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First total synthesis of type II abyssomicins: (±)-abyssomicin 2 and (±)-neoabyssomicin B†

Aleksander Canko,

^ab Georgia D. Athanassopoulou,

^a Vassilis Psycharis,

^a Catherine P. Raptopoulou,

^a Julie M. Herniman,

^c Vasileios Mouchtouris,

^d Angeliki Sofia Foscolos,

^a Elias A. Couladouros^b and Veroniki P. Vidali

*^a

Author affiliations

* Corresponding authors

^a Institute of Nanoscience & Nanotechnology, NCSR “Demokritos”, Ag. Paraskevi, Athens, Greece
E-mail: v.vidali@inn.demokritos.gr

^b Department of Food Science and Human Nutrition, Agricultural University of Athens, Athens, Greece

^c Faculty of Engineering and Physical Sciences, School of Chemistry, University of Southampton, Highfield, Southampton, UK

^d Nano-Science Center and Department of Chemistry, University of Copenhagen, Copenhagen, Denmark

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.

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DOI: https://doi.org/10.1039/D3OB00476G
Article type: Communication
Submitted: 28 Mar 2023
Accepted: 17 Apr 2023
First published: 18 Apr 2023
This article is Open Access

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Org. Biomol. Chem., 2023,21, 3761-3765

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First total synthesis of type II abyssomicins: (±)-abyssomicin 2 and (±)-neoabyssomicin B

A. Canko, G. D. Athanassopoulou, V. Psycharis, C. P. Raptopoulou, J. M. Herniman, V. Mouchtouris, A. S. Foscolos, E. A. Couladouros and V. P. Vidali, Org. Biomol. Chem., 2023, 21, 3761 DOI: 10.1039/D3OB00476G

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Organic & Biomolecular Chemistry

First total synthesis of type II abyssomicins: (±)-abyssomicin 2 and (±)-neoabyssomicin B†

Abstract

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First total synthesis of type II abyssomicins: (±)-abyssomicin 2 and (±)-neoabyssomicin B

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