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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

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posted on 2021-06-22, 18:39 authored by Luca Allievi, Sabrina Dhambri, Rongyu Sun, Mohamed Selkti, Marie-Isabelle Lannou, Geoffroy Sorin, Janick Ardisson
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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