258283-82-8Relevant articles and documents
A concise atroposelective formal synthesis of (-)-steganone
Yalcouye, Boubacar,Choppin, Sabine,Panossian, Armen,Leroux, Frédéric R.,Colobert, Fran?oise
, p. 6285 - 6294 (2014)
We describe herein the atroposelective formal synthesis of (-)-steganone, a parent member of Steganotaenia araliacea dibenzocyclooctadiene lignan lactones. Our synthesis features an atropodiastereoselective biaryl Suzuki-Miyaura cross-coupling reaction with de up to 99% using as a chiral auxiliary an enantiopure and efficiently converted β-hydroxy sulfoxide derivative. A highly atroposelective formal synthesis of (-)-steganone is described highlighting the use of an enantiopure sulfoxide as a chiral auxiliary in the Suzuki-Miyaura cross-coupling reaction.