Studies on Pillaromycin A. III. The Structure of Pillarose

Abstract

Pillarose (I), C₈H₁₂O₅, gives positive Fehling's and iodoform reactions. Absorption of an isolated carbonyl is observed in the infrared and ultraviolet region. I formed methyl pillarosides (VIIa, b) and mono-, diacetylpillaroses, and reacted with sodium borohydride to yield methyl dihydropillarosides (Xa, b). I consumed 2 moles of periodate. Periodate oxidation of I in acidic solution gave acetaldehyde, formic acid (and formaldehyde), succinaldehydic acid and carbon dioxide. From these degradation schemes and physico chemical properties of the above derivatives the structure, 2, 3, 6-trideoxy-2-glycoloylhexopyranos-4-ulose, was given to pillarose (I).