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Stereospecific synthesis of a new class of compounds: bis-homoconduritol-A, -D, and -F
Date
2005-09-05
Author
Kelebekli, L
Kara, Y
Balcı, Metin
Metadata
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Bis-homoconduritol derivatives with conduritol-A, -D, and -F structures have been synthesized starting from cyclooctatetraene. The photo oxygenation of trans-7,8-dibromo- and cis-7,8-dichlorobicyclo[4.2.0]octa-2,4-dienes afforded the bicyclic endoperoxides. Reduction of the endoperoxides with thiourea followed by acetylation gave the corresponding diacetates. The KMnO4 oxidation and epoxidation of the diacetates followed by acetylation gave the tetraacetates. Removal of the halides either with zinc-dust or Na-anthracene followed by the ammonolysis of tetraacetates afforded the bis-homoconduritol derivatives in high yield.
Subject Keywords
Cyclitols
,
Reduction
,
Oxidation
,
Bicyclic Aliphatic compounds;
,
Peroxides
,
Conduritols
URI
https://hdl.handle.net/11511/56720
Journal
CARBOHYDRATE RESEARCH
DOI
https://doi.org/10.1016/j.carres.2005.5.021
Collections
Graduate School of Natural and Applied Sciences, Article
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L. Kelebekli, Y. Kara, and M. Balcı, “Stereospecific synthesis of a new class of compounds: bis-homoconduritol-A, -D, and -F,”
CARBOHYDRATE RESEARCH
, pp. 1940–1948, 2005, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56720.