207558-13-2Relevant academic research and scientific papers
An improved dienophile-induced access to enantiopure 2,4-dideoxysugar lactones via hetero Diels-Alder reaction: Synthesis of the (+)-lactone moiety of compactin
Dujardin, Gilles,Rossignol, Sandrine,Brown, Eric
, p. 763 - 770 (2007/10/03)
Polystereocontrolled access to 4-type heterocycloadducts was consistently improved by using a new 4-oxy-substituted 1-oxabutadiene, methyl (E)-tert-butoxymethylenepyruvate (1c). Obtained in both enantiomeric forms with high diastereomerical purity, these adducts led to diprotected 2,4- dideoxyglucose 10 and -gluconolactone 12 in both L and D series in high yields. Epimerization of (-)-12 via intramolecular Mitsunobu inversion gave a straightforward access to the lactone moiety (+)-16 of compactin.
