Catalytic Asymmetric Reverse Prenylation of Indol-2-one Enabled a Synthesis of (−)-Debromoflustramine A
Yi Hou, Jiyou Huo, Ruoxin Li, Jun Hou, Pan Lei, Hongbo Wei, Weiqing Xie
Abstract
A catalytic asymmetric nucleophilic reverse prenylation of indol-2-ones in situ generated from 3-bromooxindoles with prenyltributylstannane promoted by Ni(II)/chiral N,N′ -dioxide was developed. This reaction provides facile access to C3 reverse-prenylated oxindoles in good to excellent enantioselectivities, which enabled the asymmetric synthesis of debromoflustramine A in five steps.
Topics & Concepts
ChemistryPrenylationCatalysisCombinatorial chemistryNucleophileEnantioselective synthesisStereochemistryOrganic chemistryEnzymeAsymmetric Synthesis and CatalysisAlkaloids: synthesis and pharmacologyChemical synthesis and alkaloids