Stereospecific synthesis of a new class of compounds: bis-homoconduritol-A, -D, and -F |
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Authors: | Kelebekli Latif Kara Yunus Balci Metin |
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Affiliation: | Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey. |
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Abstract: | Bis-homoconduritol derivatives with conduritol-A, -D, and -F structures have been synthesized starting from cyclooctatetraene. The photooxygenation 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 KMnO(4) 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. |
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Keywords: | Cyclitols Conduritols Peroxides Bicyclic aliphatic compounds Oxidation Reduction |
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