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Article Dans Une Revue European Journal of Organic Chemistry Année : 2017

Transition-Metal-Free Synthesis of a Known Intermediate in the Formal Synthesis of (-)-Steganacin

Résumé

The formal synthesis of both enantiomers of a natural axially chiral biaryl, steganacin is reported. The previously developed atropo-diastereoselective coupling of an aryne and an aryllithium (the 'ARYNE coupling') allows for this synthesis. In each step, the axial configuration of the biaryl could be maintained. The key intermediate of literature was accessed without using transition metals, demonstrating the interest of the ARYNE coupling as a complement or an alternative to transition metal-catalyzed couplings.

Domaines

Chimie organique
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Dates et versions

hal-02105793 , version 1 (21-04-2019)

Identifiants

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David Augros, Boubacar Yalcouye, Sabine Choppin, Matthieu Chessé, Armen Panossian, et al.. Transition-Metal-Free Synthesis of a Known Intermediate in the Formal Synthesis of (-)-Steganacin. European Journal of Organic Chemistry, 2017, 2017 (3), pp.497-503. ⟨10.1002/ejoc.201601239⟩. ⟨hal-02105793⟩
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