Stereoselective synthesis of γ-lactone fused cyclopentanoids |
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Authors: | Ay?egül Gümü? Cihangir Tanyeli |
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Institution: | Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey |
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Abstract: | The stereoselective synthesis of γ-lactone fused cyclopentanoids applying chemoenzymatic methods is described. rac-2-Hydroxymethyl-1,4,5,6-tetrachloro-7,7-dimethoxybicyclo2.2.1]hept-5-ene and rac-2-hydroxymethyl-1,4,5,6,7,7-hexachlorobicyclo2.2.1]hept-5-ene were successfully resolved by Candida rugosa lipase (CRL), to afford enantiomerically enriched products with an ee of 94 and 97%, respectively. The enantiomerically enriched acetates were then subjected to ruthenium and/or cerium catalyzed oxidation to afford α-diketones and subsequent alkaline H2O2 mediated oxidative cleavage reaction of α-diketones, followed by CH2N2 esterification, gave enantiomerically enriched γ-lactone fused cyclopentanoids with known absolute configurations. |
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