Trisequential Photooxygenation Reaction: Application to the Synthesis of Carbasugars

Date

2013-09-06

Author

BARAN, ARİF
Aydin, Gokay
Savran, Tahir
ŞAHİN, Ertan
Balcı, Metin

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4,5-Dimethylenecyclohex-1-ene was subjected to a photooxygenation reaction to introduce oxygen functionalities. The endoperoxide obtained underwent an ene-reaction to form hydroperoxides with 1,3-diene structures. Further addition of singlet oxygen to the diene units resulted in the formation of tricyclic hydroperoxides having three oxygens in the molecule. Cleavage of the oxygen-oxygen bonds followed by epoxidation of the remaining C-C double bond and concomitant ring-opening reaction furnished the isomeric carbasugars.

Subject Keywords

Products, Chemistry, Cycloaddition, Aminocyclitols, Regioselectivity, Analogs, Amino-acid, Ene-reaction, Stereoselective-synthesis, Singlet oxygen

URI

https://hdl.handle.net/11511/54130

Journal

ORGANIC LETTERS

DOI

https://doi.org/10.1021/ol401823m

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

A. BARAN, G. Aydin, T. Savran, E. ŞAHİN, and M. Balcı, “Trisequential Photooxygenation Reaction: Application to the Synthesis of Carbasugars,” ORGANIC LETTERS, pp. 4350–4353, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/54130.