Convenient preparation of a crystalline derivative of meso-tartraldehyde

Abstract

Periodate oxidation of 1,2-O-cyclohexylidenemyoinositol gives cis-3,4-cyclohexylidenedioxy-2,5-dihydroxytetrahydrofuran (III), a compound which liberates meso-tartraldehyde on mild acid hydrolysis. Condensation with nitromethane provides a synthesis of 5-nitrocyclopentane-1,2,3,4-tetraols.