4.5 Article

A Concise Atroposelective Formal Synthesis of (-)-Steganone

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2014, 期 28, 页码 6285-6294

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402761

关键词

Natural products; Cross-coupling; Biaryls; Atropoisomerism; Atroposelectivity; Diastereoselectivity; Chiral auxiliaries; Sulfoxides

资金

  1. Centre National de la Recherche Scientifique (CNRS)
  2. Ministere de l'Education Nationale et de la Recherche
  3. Malian government

向作者/读者索取更多资源

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 beta-hydroxy sulfoxide derivative.

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