A novel and short synthesis of (1,4/2)-cyclohex-5-ene-triol and its conversion to (+/-)-proto-quercitol

Date

2003-07-29

Author

Gultekin, MS
Salamci, E
Balcı, Metin

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(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.

Subject Keywords

Hydroperoxide, Endoperoxide;, Ene-reaction, Singlet oxygen, Quercitol

URI

https://hdl.handle.net/11511/57091

Journal

CARBOHYDRATE RESEARCH

DOI

https://doi.org/10.1016/s0008-6215(03)00256-8

Collections

Graduate School of Natural and Applied Sciences, Article

Citation Formats

M. Gultekin, E. Salamci, and M. Balcı, “A novel and short synthesis of (1,4/2)-cyclohex-5-ene-triol and its conversion to (+/-)-proto-quercitol,” CARBOHYDRATE RESEARCH, vol. 338, no. 16, pp. 1615–1619, 2003, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57091.