Synthetic valorization of bio-renewable resources to bioactive highly functionalized molecules

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

(−)-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.

2023-06Journal article

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