A concise atroposelective formal synthesis of (-)-steganone

Boubacar Yalcouye (1, 2) , Sabine Choppin (3) , Armen Panossian (3) , Frédéric Leroux (3) , Francoise Colobert-Leuenberger (3)

1 Substances naturelles/chimie moléculaire
2 LCM - Laboratoire de chimie moléculaire
3 LIMA - Laboratoire d'innovation moléculaire et applications

The atroposelective formal synthesis of (-)-steganone, a parent member of Steganotaenia araliacea dibenzocyclooctadiene lignan lactones, was reported. The synthesis features an atropo-diastereoselective biaryl Suzuki-Miyaura cross-coupling with ≤99% de using an enantiopure and efficiently converted β-hydroxy sulfoxide deriv. as chiral auxiliary.

Domaines: Chimie organique

Boubacar Yalcouye, Sabine Choppin, Armen Panossian, Frédéric Leroux, Francoise Colobert-Leuenberger. A concise atroposelective formal synthesis of (-)-steganone. European Journal of Organic Chemistry, 2014, 2014 (28), pp.6285-6294. ⟨10.1002/ejoc.201402761⟩. ⟨hal-02304105⟩