Synthesis of branched carbasugars via photooxygenation and manganese(III) acetate free radical cyclization

Date

2014-08-19

Author

Altun, Yasemin
Dogan, Sengul Dilem
Balcı, Metin

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Transformation of cyclohexa-1,3- and 1,4-dienes to carbasugars is described. Photooxygenation of dienes gave bicyclic endoperoxides, which were reduced with thiourea to the corresponding 1,4-dials with cis-configuration. Lactonization of the remaining double bond by oxidative addition of acetic acid to the double bond in the presence of Mn(OAc)(3) followed by lactone ring-opening reaction gave the target branched carbasugars.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/57458

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2014.05.069

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

Y. Altun, S. D. Dogan, and M. Balcı, “Synthesis of branched carbasugars via photooxygenation and manganese(III) acetate free radical cyclization,” TETRAHEDRON, pp. 4884–4890, 2014, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57458.