Stereoselective first total synthesis, confirmation of the absolute configuration and bioevaluation of botryolide-E |
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Authors: | Reddy D Kumar Shekhar V Prabhakar P Babu D Chanti Ramesh D Siddhardha B Murthy U S N Venkateswarlu Y |
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Affiliation: | a Natural Products Laboratory, Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India b Division of Biology, Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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Abstract: | 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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Keywords: | γ-Lactone Botryolide-E Jacobsen&rsquo s hydrolytic kinetic resolution (HKR) Sharpless asymmetric dihydroxylation Staphylococcus aureus Antimicrobial |
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