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
- Centre National de la Recherche Scientifique (CNRS)
- Ministere de l'Education Nationale et de la Recherche
- Malian government
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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