Synthesis of polyhydroxylated bicyclic tetrahydrofurans and tetrahydropyrans via a stereoselective domino cyclization/reduction reaction
作者: Michał MalikPiotr CmochMykhaylo A. PotopnykSławomir Jarosz
作者单位: 1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
刊名: Tetrahedron: Asymmetry, 2017, Vol.28 (12), pp.1750-1755
来源数据库: Elsevier Journal
DOI: 10.1016/j.tetasy.2017.10.001
原始语种摘要: Abstract(#br)A novel reaction cascade involving a Lewis acid-induced migration of an isopropylidene protecting group followed by the formation of a pyranose or furanose ring and subsequent reduction of the hemiacetal is described. Depending on the reaction conditions, as well as, the stereochemistry of the substrate, polyhydroxylated tetrahydrofurans or tetrahydropyrans can be obtained in reasonable yields. The synthons used in this transformation were prepared via a highly stereoselective one-pot tandem reaction, consisting of a 1,4-Michael addition of vinylmagnesium bromide to d -glucose-derived cyclohexenone followed by aldol reaction with 2,3- O -isopropylidene- d -glyceraldehyde.
全文获取路径: Elsevier  (合作)
影响因子:2.115 (2012)

  • cyclization 环化
  • reaction 反酌
  • bicyclic 二环的
  • domino 多米诺
  • reduction 减少