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Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2023

Total synthesis of the natural (−)-205B alkaloid and its activity toward α7 nAChRs

Résumé

A new approach to the synthesis of the (−)-205B alkaloid is described in this paper. This work is characterised by the development of an efficient chirality transfer through a silyl tethered intramolecular alkylation reaction, an unprecedented tandem highly selective iridium catalyzed partial reduction of lactam coupled with an acid promoted aza-Prins reaction, and an almost complete stereochemical control in Shenvi's radical hydrogen atom transfer on an exocyclic methylene. The second part of this work demonstrates the positive allosteric behavior of this natural alkaloid toward α7 nAChRs, in contrast to the reported inhibitory effect of the unnatural enantiomer.
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hal-03959309 , version 1 (17-10-2023)

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Sara Mazeh, M Dolores Garcia-Fernandez, Barbara Pelletier, Christophe J Moreau, Philippe Delair. Total synthesis of the natural (−)-205B alkaloid and its activity toward α7 nAChRs. Organic & Biomolecular Chemistry, 2023, 21 (4), pp.817-822. ⟨10.1039/d2ob01723g⟩. ⟨hal-03959309⟩
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