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Total syntheses of KS-501, KS-502, and their enantiomers

RG Dushin, SJ Danishefsky

文献索引：Dushin; Danishefsky Journal of the American Chemical Society, 1992 , vol. 114, # 2 p. 655 - 659

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被引用次数: 77

摘要

Abstract: The total syntheses of the title compounds are described. The key step involves the coupling of the anhydrofuranose 18 (as well as its enantiomer) with salicylate derivative 17 under the influence of potassium carbonate. Both the epoxidation of 7 (achieved with 2, 2- dimethyldioxirane) and the glycosylation of 17 appear to be stereospecific.

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2,2-dimethyl-5-(1-heptyl)-7-hydroxy-4H-1,3-benzodioxin-4-one结构式

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7-(Benzyloxy)-5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one结构式

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4-[2-[(2S,3R,4R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-6-heptyl-4-hydroxybenzoyl]oxy-2-heptyl-6-hydroxybenzoic acid结构式

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~%

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~%

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~%

4-[2-[(2S,3R,4R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-6-heptyl-4-hydroxybenzoyl]oxy-2-heptyl-6-hydroxybenzoic acid结构式

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