The first and stereoselective synthesis of 8-azidocyclooct-4-ene-1,3,6-triol
Tetrahedron, vol.199, 2026 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 199
- Publication Date: 2026
- Doi Number: 10.1016/j.tet.2026.135359
- Journal Name: Tetrahedron
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, BIOSIS, Chemical Abstracts Core, Chimica, EMBASE, Academic Search Ultimate (EBSCO)
- Keywords: Aminocyclitols, Azides, Azidocyclooctenetriol, Cyclooctadiene epoxide, Epoxy endoperoxide
- Ataturk University Affiliated: Yes
Abstract
Cyclooctadiene epoxide was used as key compound for the first efficient synthesis of 8-azidocyclooctenetriacetate. Photooxygenation of the cyclooctadiene epoxide, prepared by epoxidation of 1,2-dibromocyclooctene followed by elimination with DBU for further functionalization, gave cyclooctene epoxy endoperoxide as a single isomer in high yield. Reduction of endoperoxide with thiourea and reaction of the corresponding epoxy-diol with NaN3 followed by acetylation provided the target, 8-azidocyclooctenetriol, as the sole product. The structure of its was determined via by 1D and 2D NMR spectroscopy.