A Concise Atroposelective Formal Synthesis of (–)‐Steganone. Issue 28 (21st August 2014)

• Record Type: Journal Article
• Authors: Yalcouye, Boubacar; Choppin, Sabine; Panossian, Armen; Leroux, Frédéric R.; Colobert, Françoise
• Is Part Of: European journal of organic chemistry. Issue 28(2014)
• Page Start: 6285
• Page End: 6294
• Publication Date: 2014-08-21
• Subjects: Natural products -- Cross‐cou­pling -- Biaryls -- Atropoisomerism -- Atroposelectivity -- Diastereoselectivity -- Chiral auxiliaries -- Sulfoxides; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402761
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : 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.