A concise and stereospecific synthesis of some cyclitols containing eight-membered rings: cyclooctane-1,2,3,4-tetraoles
Özet
A concise and efficient synthesis of cyclooctane-1,2,3,4-tetraoles, new polyhydroxylated eight-membered carbocycles, is described starting from cis,cis-1,3-cyclooctadiene. Cyclooctene endoperoxide obtained by photooxygenation of cis,cis-1,3-cyclooctadiene was the key compound in the synthesis. Reduction of the endoperoxide with zinc or thiourea followed by acetylation of the hydroxyl group and OsO4/NMO oxidation of the double bond gave (1R(S),2S(R),3R(S),4S(R))-cyclooctane-1,2,3,4-tetraol. Interestingly, epoxidation of cyclooctene-1,4-diol with m-CPBA also afforded trans-epoxy-diol 17. (1R(S),2R(S),3R(S),4S (R))-cyclooctane-1,2,3,4-tetraol was easily obtained by hydrolysis of epoxy-diol 17. (C) 2010 Elsevier Ltd. All rights reserved.
Anahtar kelimeler
Atıf için künye
Salamcı, E. (2010). A concise and stereospecific synthesis of some cyclitols containing eight-membered rings: cyclooctane-1,2,3,4-tetraoles. TETRAHEDRON, 66(23), 4010–4015. https://doi.org/10.1016/j.tet.2010.04.052
BibTeX
@article{salamci2010-71000,
author = {Salamcı, Emine},
title = {A concise and stereospecific synthesis of some cyclitols containing eight-membered rings: cyclooctane-1,2,3,4-tetraoles},
journal = {TETRAHEDRON},
year = {2010},
volume = {66},
number = {23},
pages = {4010--4015},
issn = {0040-4020},
doi = {10.1016/j.tet.2010.04.052},
url = {https://akademik.atauni.edu.tr/yayinlar/71000-a-concise-and-stereospecific-synthesis-of-some-cyclitols-containing-eight}
}