Stereospecific synthesis of a new class of aminocyclitol with the conduramine D-2 configuration

Date

2006-09-25

Author

Kelebekli, Latif
Celik, Murat
Sahin, Ertan
Kara, Yunus
Balcı, Metin

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A new aminocyclitol derived from bicyclo[4.2.0(1,6)]octane was synthesized starting from cyclooctatetraene. Photooxygenation of trans-7,8-diacetoxy-bicyclo[4.2.0]octa-2,4-diene afforded a bicyclic endoperoxide. Reduction of the endoperoxide with thiourea followed by a palladium-catalyzed ionization/cyclization reaction gave an oxazolidinone derivative. Oxidation of the double bond in the oxazolidinone with KNlnO(4) followed by acetylation gave the oxazolidinone-tetraacetate whose exact configuration was determined by X-ray diffraction analysis. Hydrolysis of the oxazolidinone ring and removal of the acetate groups furnished the desired aminocyclitol.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/56868

Journal

TETRAHEDRON LETTERS

DOI

https://doi.org/10.1016/j.tetlet.2006.07.108

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

L. Kelebekli, M. Celik, E. Sahin, Y. Kara, and M. Balcı, “Stereospecific synthesis of a new class of aminocyclitol with the conduramine D-2 configuration,” TETRAHEDRON LETTERS, pp. 7031–7035, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56868.