The first and stereoselective synthesis of 8-azidocyclooct-4-ene-1,3,6-triol
Özet
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.
Anahtar kelimeler
Atıf için künye
Salamcı, E., & Kilic Lafzi, A. (2026). The first and stereoselective synthesis of 8-azidocyclooct-4-ene-1,3,6-triol. TETRAHEDRON, 199. https://doi.org/10.1016/j.tet.2026.135359
BibTeX
@article{salamci2026-71020,
author = {Salamcı, Emine and Kilic Lafzi, Ayse},
title = {The first and stereoselective synthesis of 8-azidocyclooct-4-ene-1,3,6-triol},
journal = {TETRAHEDRON},
year = {2026},
volume = {199},
issn = {0040-4020},
doi = {10.1016/j.tet.2026.135359},
url = {https://akademik.atauni.edu.tr/yayinlar/71020-the-first-and-stereoselective-synthesis-of-8-azidocyclooct-4-ene-136-triol}
}