1,8-Diazabicyclo[5.4.0]undec-7-ene-Promoted Oxidation by Atmospheric Oxygen of an Allylsilane Derived from γ-Formyl-Substituted Cyclopentene

Development of a new approach for the synthesis of (+)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester based on the [2+2]-cycloadduct of 5-trimethylsilylcyclopentadiene and dichloroketene

“…In this regard, an illustrative example can be seen in trying to epimerize the aldehyde group in compound 16 by treatment with DBU in boiling toluene, which unexpectedly led to the product of oxidation by air oxygen 19 . 23…”

“…In this regard, an illustrative example can be seen in trying to epimerize the aldehyde group in compound 16 by treatment with DBU in boiling toluene, which unexpectedly led to the product of oxidation by air oxygen 19. 23 Thus, we chose the more promising alcohol 14 and its aldehyde 17. This was due to the higher stability of compound 17 and to the possibility of its use in homologation reactions.…”