Gold(I)-catalyzed 7-exo-dig Cyclization: A Key Step to Access the Bicyclo[4.2.1]nonane Skeleton of Vibsatin A, a Neurotrophic Diterpenoid - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2021

Gold(I)-catalyzed 7-exo-dig Cyclization: A Key Step to Access the Bicyclo[4.2.1]nonane Skeleton of Vibsatin A, a Neurotrophic Diterpenoid

Résumé

Vibsatin A is a new neurotrophic vibsane-type diterpenoid comprising a bridged bicyclo[4.2.1]nonane skeleton. Inspired by Sawamura’s works, we generated the bicyclic backbone through a Conia-ene-derived 7-exo-dig cyclization from an enantiomerically enriched TIPS-based silyl enol ether. The reaction, catalyzed by a sensitive gold(I) complex, was efficiently performed on a large scale by glovebox free techniques. Furthermore, the shape of this system was exploited for subsequent installation of all of the stereogenic centers.
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hal-03366083 , version 1 (05-10-2021)

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Luca Allievi, Sabrina Dhambri, Rongyu Sun, Mohamed Selkti, Marie-Isabelle Lannou, et al.. Gold(I)-catalyzed 7-exo-dig Cyclization: A Key Step to Access the Bicyclo[4.2.1]nonane Skeleton of Vibsatin A, a Neurotrophic Diterpenoid. Organic Letters, 2021, 23 (13), pp.5218-5222. ⟨10.1021/acs.orglett.1c01757⟩. ⟨hal-03366083⟩
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