ChemInform Abstract: (2,3)Wittig Rearrangement on Carbohydrate Template. Novel Approach to Chiral Synthesis of 3‐Alkylmalic Acids.

Abstract

The ketone (I) derived from a furanoside is reductively alkynylated with the lithium acetylide (II) to produce the alkynylfuranoside (III) which is hydrogenated or reduced and then etherified with the bromoacetate (IV), yielding selectively the Z‐ or E‐configurated alkenyl derivative (Va) or (Vb).