A novel and stereospecific synthesis of aminocyclitol: N-tosyldihydroconduramine E2
Özet
A stereospecific synthesis of N-tosyldihydroconduramine E2, a new aminocyclitol, has been synthesised starting from cyclohexa-1,3-diene. The photooxygenation of cyclohexa-1,3-diene afforded the bicyclic endoperoxide. Reduction of the endoperoxide with thiourea and then reaction of the bis-carbamate with p-TsNCO followed by a palladium-catalysed ionisation/cyclisation reaction, gave a vinyl oxazolidin-2-one. Oxidation of the double bond in the oxazolidin-2-one with KMnO(4) followed by acetylation, gave the oxazolidinone-diacetates. Hydrolysis of the oxazolidinone ring and removal of the acetate groups gave the desired aminocyclitol, N-tosyldihydroconduramine E2.
Anahtar kelimeler
Atıf için künye
Kelebekli, L., Çelik, M., & Kara, Y. (2010). A novel and stereospecific synthesis of aminocyclitol: N-tosyldihydroconduramine E2. JOURNAL OF CHEMICAL RESEARCH(1), 54–56. https://doi.org/10.3184/030823410x12628681698796
BibTeX
@article{kelebekli2010-71783,
author = {Kelebekli, Latif and Çelik, Murat and Kara, Yunus},
title = {A novel and stereospecific synthesis of aminocyclitol: N-tosyldihydroconduramine E2},
journal = {JOURNAL OF CHEMICAL RESEARCH},
year = {2010},
number = {1},
pages = {54--56},
issn = {1747-5198},
doi = {10.3184/030823410x12628681698796},
url = {https://akademik.atauni.edu.tr/yayinlar/71783-a-novel-and-stereospecific-synthesis-of-aminocyclitol-n-tosyldihydroconduramine}
}