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KMID : 1059519960400110692
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Journal of the Korean Chemical Society
1996 Volume.40 No. 11 p.692 ~ p.698
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Synthetic Studies on Discokiolide B
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Kim Hong-Seok
Kim Sang-Hwa
Lee Ju-Young
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Abstract
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A synthesis of the oxazole skeleton of discokiolide B, represented by discokiic acid 1, is described. Aldol condensation of 2[2'-(4-phenyl-3-butenyl)]-1,3-oxazole 4-carboxaldehyde(4a) with lithium enolate of methyl propionate provided the discokiic acid methyl ester. The key intermediate 2[2'-(4-phenyl-3-butenyl)]-1,3-oxazole-4-carboxaldehyde (4a) has been synthesized from the rhodium-catalyzed cycloaddition of diazomalonaldehyde with nitrile. The relative stereochemistry of the 3-hydroxy-2-methylpropanoate unit of discokiic acid was assigned on the basis of 1H and 13C NMR data.
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