A CONCISE AND CONVENIENT SYNTHESIS OF DL-PROTO-QUERCITOL AND DL-GALA-QUERCITOL VIA ENE REACTION OF SINGLET OXYGEN COMBINED WITH [2-CYCLOADDITION TO CYCLOHEXADIENE(4])

Authors
SALAMCI E SECEN H SUTBEYAZ Y BALCI M
Citation
E. Salamci et al., A CONCISE AND CONVENIENT SYNTHESIS OF DL-PROTO-QUERCITOL AND DL-GALA-QUERCITOL VIA ENE REACTION OF SINGLET OXYGEN COMBINED WITH [2-CYCLOADDITION TO CYCLOHEXADIENE(4]), Journal of organic chemistry, 62(8), 1997, pp. 2453-2457
Citations number
48
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
8
Year of publication
1997
Pages
2453 - 2457
Database
ISI
SICI code
0022-3263(1997)62:8<2453:ACACSO>2.0.ZU;2-P
Abstract
Photooxygenation of 1,4-cyclohexadiene afforded hydroperoxy endoperoxi des 3 and 4 in a ratio of 88:12. Reduction of 3 with LiAlH4 or thioure a followed by acetylation of the hydroxyl group and KMnO4 oxidation of the double bond gave proto-quercitol 10b. Application of the same rea ction sequences to 4 resulted in the formation of gala-quercitol 14. Q uercitols were easily obtained by ammonolysis of acetate derivatives i n MeOH. The outcome of dihydroxylation reactions were supported by con formational analysis.