Catalytic enantioselective conjugate addition en route to paxilline indoloterpenoids. Issue 24 (14th June 2019)

• Record Type: Journal Article
• Authors: Schatz, Devon J.; Li, Wenqin; Pronin, Sergey V.
• Is Part Of: Tetrahedron. Volume 75:Issue 24(2019)
• Page Start: 3361
• Page End: 3365
• Publication Date: 2019-06-14
• Subjects: Cyclopentenone -- Grignard reagent -- Conjugate addition -- Enantioselective -- Catalytic -- Natural products -- Synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.04.076
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Development of enantioselective synthesis of precursor en route to paxilline indoloterpenoids is described. Evaluation of 25 diphosphine-based ligands has led to identification of JosiPhos derivative that allows for asymmetric conjugate addition of homoprenyl Grignard reagent to 2-methylcyclopent-2-en-1-one in excellent yield and with appreciable levels of enantioinduction. Application to the conjugate addition of other Grignard reagents is demonstrated. Graphical abstract: Image 1