To achieve the synthesis of azasugar derivatives with the utilization of singlet oxygen, pyridine was used as the starting material. The reduction of pyridine followed by a singlet oxygen reaction afforded cyclic aza-endoperoxides (14 and 16). However, many attempts were made to convert the aza-endoperoxides to the corresponding di- and triacetates without success. However, the base-catalyzed rearrangement of 14 gave unprecedented rearrangement products 23 and 24.
SALAMCI, EMİNE; BAYRAM, BEYHAN; and BALCI, METİN (2006) "Chemistry of Bicyclic Endoperoxides Derived from Dihydropyridine Derivatives: Attempted Synthesis of Polyhydroxypiperidine Derivatives," Turkish Journal of Chemistry: Vol. 30: No. 4, Article 4. Available at: https://journals.tubitak.gov.tr/chem/vol30/iss4/4