From Pyridine to (-)-Agelastatin A

Vale, João R.; Fortunato, Milene A. G.; Andrade, Késsia H. S.; Rocha, Ângelo M. R.; Afonso, Carlos; Siopa, Filipa

http://hdl.handle.net/10451/61993

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Autores

Vale, João R.

Fortunato, Milene A. G.

Andrade, Késsia H. S.

Rocha, Ângelo M. R.

Afonso, Carlos

Siopa, Filipa

Resumo(s)

(−)-Agelastatin A was synthetized employing a flow photorearrangement of a pyridinium salt, constructing in one step the cyclopentene core possessing the desired functionalities and relative configurations. A flow enzymatic kinetic resolution of the resulting bicyclic vinyl aziridine delivered the enantiopure precursor to the natural product. This total synthesis required the use of a single protective group. Two novel agelastatin N3-derivatives were synthesized and their cytotoxicity evaluated against a series of cancer cell lines, which corroborated the importance of unsubstituted N3 in the biological activity of (−)-agelastatin A.

Descrição

© 2023 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cite.

URI

http://hdl.handle.net/10451/61993

Citação

Vale JR, Fortunato MAG, Andrade KHS, Rocha ÂMR, Afonso CAM, Siopa F. From pyridine to (−)‐agelastatin a. Adv Synth Catal [Internet]. 4 de julho de 2023;365(13):2240–7. Disponível em: https://onlinelibrary.wiley.com/doi/10.1002/adsc.202300560