80127-52-2Relevant academic research and scientific papers
Preparation of a Chiral Lactone from Leavoglucosan; a Key Intermediate for Synthesis of the Spiroacetal Moietes of the Avermectins and Milbemycins
Baker, Raymond,Boyes, R. Hugh O.,Broom, D. Mark P.,O'Mahony, Mary J.,Swain, Christopher J.
, p. 1613 - 1622 (2007/10/02)
A synthesis of two diprotected (4S,6S)-4-hydroxy-6-hudroxymethyltetrahydropyran-2-ones has been developed from laevoglucosan.Reaction of these lactones with a substituted chiral lithium acetylide followed by hydrogenation and acid-catalysed cyclisation led to formation of the spiroacetal moiety of milbemycin α1 and α3.The acetylene was prepared by resolution of racemic material obtained from reaction of lithium acetylide and cis-butene epoxide.Alternatively a stereocontrolled synthesis was developed from (S)-methyl-3-hydroxy-2-methylpropionate which involved 'chelation controlled' addition of lithium dimethylcuprate to the corresponding tetrahydropyranyloxy aldehyde.
A Nitrile Oxide Based Entry to 2,3-Dihydropyran-4-ones. Synthesis of a Protected Version of "Compactin Lactone" in Racemic and Optically Active Forms
Kozikowski, Alan P.,Li, Chun-Sing
, p. 778 - 785 (2007/10/02)
The use of nitrile oxides bearing a masked β-oxo group as β-hydroxy-3-oxopropionylating agents for the vicinal functionalization of olefins is described.The β-hydroxy ketones revealed on hydrogenation of the initially formed 1,3-dipolar cycloaddition prod
The Chemistry of Spiroacetals. Preparation of a Chiral Disubstituted Lactone Derivative; a Key Intermediate for Synthesis of the Spiroacetal Moieties of the Avermectins and Milbemycins
Baker, Raymond,Boyes, R. Hugh O.,Broom, D. Mark P.,Devlin, J. Alastair,Swain, Christopher J.
, p. 829 - 831 (2007/10/02)
A synthesis of two diprotected (4S,6S)-4-hydroxy-6-hydroxymethyltetrahydropyran-2-ones has been developed from laevoglucosan; reaction of these lactones with a substituted lithium acetylide derivative followed by hydrogenation and acid catalysed cyclisati
