Antiinflammatory 2,3-dihydro-1H-pyrrolizines, IX: Synthesis and oxidation of (2,3-dihydro-6,7-diphenyl-1H-pyrrolizin-5-yl)acetaldehyde (DADHP-5-acetaldehyde)

Article abstract of DOI:10.1002/ardp.19863190605

The pyrrolizinyl substituted oxalic acid derivatives 1a or 1b are reduced to the diol 2, which on acidic hydrolysis given the title compound 3. PDC oxidation of the pyrrolizinylacetaldehyde 3 results in the degradation of the side chain at C-5 to yield the aldehyde 5 and the lactam 6. The diol 2 shows weak antiinflammatory activity.