Turkish Journal
of
Chemistry
chem@tubitak.gov.tr
Turkish Journal of Chemistry
Chemistry of Bicyclic Endoperoxides Derived from Dihydropyridine Derivatives: Attempted Synthesis of Polyhydroxypiperidine DerivativesMetin BALCI2,
1Department of Chemistry, Atatürk University, 25240 Erzurum-TURKEY
2Department of Chemistry, Middle East Technical University,
06531 Ankara-TURKEY
e-mail: esalamci@atauni.edu.tr, mbalci@metu.edu.tr
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 aza-endoperoxides to the corresponding di- and triacetates without success. However, the base-catalyzed rearrangement of 14 gave unprecedented rearrangement products 23 and 24.
Key Words: Azasugar derivatives, amino sugars, singlet oxygen, bicyclic endoperoxides
Turk. J. Chem., 30, (2006), 441-449.
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Other articles published in the same issue: Turk. J. Chem.,vol.30,iss.4.