The above results suggested that the C4 alcohol was too hindered for successful elimination. Attempts to alter the pucker of the cyclopentane via oxidation of the C3 alcohol to 29 were attempted (Scheme 7B). Exposure to DMP gave only 1,2-diol scission to 25, even in the presence of pyridine. Oxidation with IBX to avoid scission gave only recovered 24; 34 SO3-pyridine also returned only 24. Despite a similar Swern oxidation reported by Johnson, 24 in only decomposition under these conditions.