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

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

Org Biomol Chem. 2023 May 10;21(18):3761-3765. doi: 10.1039/d3ob00476g.

Authors

Aleksander Canko^{1

2}, Georgia D Athanassopoulou¹, Vassilis Psycharis¹, Catherine P Raptopoulou¹, Julie M Herniman³, Vasileios Mouchtouris⁴, Angeliki Sofia Foscolos¹, Elias A Couladouros², Veroniki P Vidali¹

Affiliations

¹ Institute of Nanoscience & Nanotechnology, NCSR "Demokritos", Ag. Paraskevi, Athens, Greece. v.vidali@inn.demokritos.gr.
² Department of Food Science and Human Nutrition, Agricultural University of Athens, Athens, Greece.
³ Faculty of Engineering and Physical Sciences, School of Chemistry, University of Southampton, Highfield, Southampton, UK.
⁴ Nano-Science Center and Department of Chemistry, University of Copenhagen, Copenhagen, Denmark.

PMID: 37083981
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.