A novel and short synthesis of (1,4/2)-cyclohex-5-ene-triol and its conversion to (+/-)-proto-quercitol
Özet
(1,4/2)-Cyclohex-5-ene-triol was synthesized starting from cyclohexa-1,4-diene with two different approaches. Photooxygenation of cyclohexa-1,4-diene and epoxy-cyclohexene afforded anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide and anti-7-oxabicclo[4.1.0]hept-4-en-3-yl hydroperoxide, respectively. Hydroperoxy endoperoxide was reduced with aqueous sodium bisulfite; hydroperoxy-epoxide with dimethylsulfide-titanium tetraisopropoxide to give 7-oxabicyclo[4.1.0]hept-4-en-3-ol. Acidic hydrolysis of the epoxy-alcohol gave the (1,4/2)-cyclohex-3-ene-triol. Oxidation of the double bond with KMnO4 resulted in the formation of proto-quercitol. (C) 2003 Elsevier Ltd. All rights reserved.
Anahtar kelimeler
Atıf için künye
Gültekin, M. S., Salamcı, E., & BALCI, M. (2003). A novel and short synthesis of (1,4/2)-cyclohex-5-ene-triol and its conversion to (+/-)-proto-quercitol. CARBOHYDRATE RESEARCH, 338(16), 1615–1619. https://doi.org/10.1016/s0008-6215%2803%2900256-8
BibTeX
@article{gultekin2003-70486,
author = {Gültekin, Mehmet Serdar and Salamcı, Emine and BALCI, Metin},
title = {A novel and short synthesis of (1,4/2)-cyclohex-5-ene-triol and its conversion to (+/-)-proto-quercitol},
journal = {CARBOHYDRATE RESEARCH},
year = {2003},
volume = {338},
number = {16},
pages = {1615--1619},
issn = {0008-6215},
doi = {10.1016/s0008-6215(03)00256-8},
url = {https://akademik.atauni.edu.tr/yayinlar/70486-a-novel-and-short-synthesis-of-142-cyclohex-5-ene-triol-and-its-conversion-to}
}