A concise and convenient synthesis of DL-proto-quercitol and DL-gala-quercitol via ene reaction of singlet oxygen combined with [2+4] cycloaddition to cyclohexadiene
Özet
Photooxygenation of 1,4-cyclohexadiene afforded hydroperoxy endoperoxides 3 and 4 in a ratio of 88:12. Reduction of 3 with LiAlH4 or thiourea followed by acetylation of the hydroxyl group and KMnO4 oxidation of the double bond gave proto-quercitol 10b. Application of the same reaction sequences to 4 resulted in the formation of gala-quercitol 14. Quercitols were easily obtained by ammonolysis of acetate derivatives in MeOH. The outcome of dihydroxylation reactions were supported by conformational analysis.
Atıf için künye
Salamcı, E., Seçen, H., SUTBEYAZ, Y., & BALCI, M. (1997). A concise and convenient synthesis of DL-proto-quercitol and DL-gala-quercitol via ene reaction of singlet oxygen combined with [2+4] cycloaddition to cyclohexadiene. JOURNAL OF ORGANIC CHEMISTRY, 62(8), 2453–2457.
BibTeX
@article{salamci1997-71008,
author = {Salamcı, Emine and Seçen, Hasan and SUTBEYAZ, Yaşar and BALCI, Metin},
title = {A concise and convenient synthesis of DL-proto-quercitol and DL-gala-quercitol via ene reaction of singlet oxygen combined with [2+4] cycloaddition to cyclohexadiene},
journal = {JOURNAL OF ORGANIC CHEMISTRY},
year = {1997},
volume = {62},
number = {8},
pages = {2453--2457},
issn = {0022-3263},
url = {https://akademik.atauni.edu.tr/yayinlar/71008-a-concise-and-convenient-synthesis-of-dl-proto-quercitol-and-dl-gala-quercitol}
}