Dispiroketals in synthesis. Part 25. Further reactions of dispiroketal protected glycolate to afford optically active 1,2,3,4-tetraols

Glycolic acid can be converted to optically active 1,2,3,4-tetraols using a dispiroketal unit as a protecting group and chiral auxiliary. Aldol reacti ons of dispiroketal protected glycolate with aldehydes afford one diastereo isomer preferentially with two newly formed stereogenic centres. To extend the polyol chain, the carbonyl group of the aldol product is converted to a vinyl ether by the Tebbe reagent after protection of the free alcohol. A s ubsequent hydroboration-oxidation protocol affords the dispiroketal protect ed tetraol. The final deprotection of the tetraol occurs selectively withou t epimerisation or migration of the silyloxy protecting groups.