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

Salamci, Emine
Bayram, Beyhan
Balcı, Metin
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.


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IChiral 1,2-amino alcohols were synthesized via newly developed “intramolecular unsaturation transfer” using cyclohexanone, propargyl bromide, and various chiral amino alcohols as starting components. These amino alcohols can be potential chiral ligands for many asymmetric transformation reactions. Therefore, their effectiveness as chiral ligands in diethylzinc addition to benzaldehyde and N-diphenylphosphinoyl imines were tested. Various parameters including temperature, solvent, ligand amount etc. were sc...
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Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton
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1,3,3a,7a-Tetrahydro-2-benzofuran was used as key compound for the synthesis of various bishomoinositol derivatives. The diene was subjected to an epoxidation reaction for further functionalization of the diene unit. The bisepoxide obtained was submitted to a ring-opening reaction with acid in the presence of water. Various bishomoinositols were synthesized. However, when the reaction was carried out in the presence of acetic anhydride, a substituted 3-oxabicyclo[3.3.1]nonane skeleton was formed. The mechan...
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The oxidation of some alkoxy tropone and tropone ketal derivatives with singlet oxygen and m-chloroperbenzoic acid was investigated. In most cases furan and furanoid derivatives were isolated. The structures of the formed products were determined by means of spectral data and the formation mechanism of these unusual products is discussed.
Citation Formats
E. Salamci, B. Bayram, and M. Balcı, “Chemistry of bicyclic endoperoxides derived from dihydropyridine derivatives: Attempted synthesis of polyhydroxypiperidine derivatives,” TURKISH JOURNAL OF CHEMISTRY, pp. 441–449, 2006, Accessed: 00, 2020. [Online]. Available: