A simple, first stereoselective total synthesis of botryolide-E has been described. The synthesis started from propylene oxide employing Jacobsen's hydrolytic kinetic resolution (HKR), selective epoxide opening, sharpless asymmetric dihydroxylation, one pot acetonide deprotection and lactonization as key steps. Further, the synthesis confirms the absolute configuration of the natural product botryolide-E and we evaluated the biological behavior of natural product botryolide-E against a panel of bacteria and fungi. Botryolide-E exhibits significant potent activity against Staphylococcus aureus (MTCC 96) (6.25 μg/ml), good against Escherichia coli (MTCC 443) (12.5 μg/ml), Bacillus subtilis (MTCC 441) (25 μg/ml) and compound 1 exhibited good to moderate antifungal activity.
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【Stereoselective first total synthesis, confirmation of the absolute configuration and bioevaluation of botryolide-E.].
【立体选择性首次全合成，确定了botryoolide-E的绝对构型和生物评估。】
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DOI：10.1016/j.bmcl.2010.12.024文章类型：杂志文章
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已经描述了一种简单的，首次立体选择性的botryoolide-E全合成。该合成从环氧丙烷开始，采用Jacobsen水解动力学拆分 (HKR)，选择性环氧开放，sharpless不对称二羟基化，一锅丙酮脱保护和内酯化作为关键步骤。此外，该合成证实了天然产物botryoolide-E的绝对构型，并且我们评估了天然产物botryoolide-E对一组细菌和真菌的生物学行为。葡萄糖醇内酯-E对金黄色葡萄球菌 (mtcc96) (6.25 μ g/ml) 表现出显著的有效活性，对大肠杆菌 (MTCC 443) (12.5 μ g/ml)，枯草芽孢杆菌 (MTCC 441) (25 μ g/ml) 表现出良好的抗真菌活性，化合物1表现出良好至中等的抗真菌活性。
