Stereospecific synthesis of a DL-gala-aminoquercitol derivative

Date

2010-05-08

Author

KURBANOĞLU, NAMUDAR İZZET
ÇELİK, Murat
KILIÇ, Hamdullah
Alp, Cemalettin
ŞAHİN, Ertan
Balcı, Metin

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A new aminoquercitol derivative was synthesized starting from 1,4-cyclohexadiene. Photooxygenation of cyclohexa-1,4-diene afforded anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxicle as the main product. The formed hydroperoxy endoperoxide was reduced with LiAlH(4) to produce anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol. Protection of alcohol with acetyl chloride followed by reduction of the endoperoxide with thiourea, and then palladium-catalyzed ionization/cyclization reaction gave an oxazolidinone derivative. Hydrolysis of the oxazolidinone ring and acetylation gave an amino compound. Oxidation of the double bond in the amino compound with OsO(4) followed by acetylation gave the amino tetraacetate and removal of the acetate groups furnished the desired aminoquercitol whose exact configuration was determined by X-ray diffraction analysis.

Subject Keywords

Cyclitols, Oxazolidinone, Aminoquercitols, Endoperoxide, X-ray analysis

URI

https://hdl.handle.net/11511/50476

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2010.03.028

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

N. İ. KURBANOĞLU, M. ÇELİK, H. KILIÇ, C. Alp, E. ŞAHİN, and M. Balcı, “Stereospecific synthesis of a DL-gala-aminoquercitol derivative,” TETRAHEDRON, pp. 3485–3489, 2010, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/50476.