Resolution of (+/-)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: synthesis of (-)- and (+)-proto-quercitol
Özet
Photooxygenation of cyclohexa-1,4-diene afforded anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide. The hydroperoxy endoperoxide was reduced with dimethylsulfide-titanium tetraisopropoxide to produce ()-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol. The highly efficient enantioselective resolution of the racemic (+/-)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol was accomplished with Candida cylindracea lipase (CCL) to produce the enantiomerically enriched alcohol and the corresponding acetate: The cleavage of the peroxide linkage by thiourea followed by the oxidation of the double bond with OsO4 resulted in the formation of (-)-proto-quercitol and (+)-proto-quercitol, respectively. (C) 2003 Elsevier Ltd. All rights reserved.
Atıf için künye
Gültekin, M. S., Çelik, M., TURKUT, E., TANYELI, C., & BALCI, M. (2004). Resolution of (+/-)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: synthesis of (-)- and (+)-proto-quercitol. TETRAHEDRON-ASYMMETRY, 15(3), 453–456. https://doi.org/10.1016/j.tetasy.2003.11.037
BibTeX
@article{gultekin2004-70494,
author = {Gültekin, Mehmet Serdar and Çelik, Murat and TURKUT, E and TANYELI, C and BALCI, M},
title = {Resolution of (+/-)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: synthesis of (-)- and (+)-proto-quercitol},
journal = {TETRAHEDRON-ASYMMETRY},
year = {2004},
volume = {15},
number = {3},
pages = {453--456},
issn = {0957-4166},
doi = {10.1016/j.tetasy.2003.11.037},
url = {https://akademik.atauni.edu.tr/yayinlar/70494-resolution-of-anti-23-dioxabicyclo222oct-7-en-5-ol-via-candida-cylindracea}
}