Chemistry of bicyclic endoperoxides derived from dihydropyridine derivatives: Attempted synthesis of polyhydroxypiperidine derivatives

Salamci E., Bayram B., Balci M.

TURKISH JOURNAL OF CHEMISTRY, vol.30, no.4, pp.441-449, 2006 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 30 Issue: 4
  • Publication Date: 2006
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.441-449
  • Middle East Technical University Affiliated: No

Abstract

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 azaendoperoxides to the corresponding di- and triacetates without success. However, the base-catalyzed rearrangement of 14 gave unprecedented rearrangement products 23 and 24.