107692-05-7Relevant academic research and scientific papers
Enantioselective total synthesis and structure determination of the antiherpetic anthrapyran antibiotic AH-1763 IIa
Tietze, Lutz F.,Gericke, Kersten M.,Singidi, Ramakrishna Reddy
, p. 6990 - 6993 (2007/10/03)
(Chemical Equation Presented) The antiherpetic anthrapyran antibiotic (14S,16R)-AH-1763 IIa (see right-hand structure) and its (14R,16R) diastereomer have been prepared in enantioselective total syntheses. The relative and absolute stereochemistry of the
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 FORMAL SYNTHESIS OF (+)MILBEMYCIN β3: A WITTIG APPROACH
Baker, Raymond,O'Mahony, Mary J.,Swain, Christopher J.
, p. 3059 - 3062 (2007/10/02)
A new route has been established to generate the C14-C15 trisubstituted double bond of milbemycin β3 by reaction of a Wittig reagent with the appropriate spiroacetal aldehyde.The product of this reaction, after conversion to the iodide and enan
