Abstract
The racemic 7-methyl-7-hydroxy-2,3-benzo[c]octa-1,6-olide, the analog of natural product (6R)-3,7-dimethyl-7-hydroxy-2-octen-1,6-olide, was totally synthesized using easily available (E)-2-(2-carboxyvinyl)benzoic acid as a raw material in nine-step reactions including three key steps of Wittig reaction, epoxidation, and cyclization, with an overall yield of 10.3%. The bioassay results showed that ( ± )-2 exhibited stronger antifungal activity than the natural product ( ± )-1 and (R)-1 against Alternaria solani with an EC₅₀ value of 27.36 μg/ml.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alternaria / drug effects*
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Antifungal Agents / chemical synthesis*
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Antifungal Agents / chemistry
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Antifungal Agents / pharmacology*
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Biological Products / chemical synthesis*
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Biological Products / chemistry
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Biological Products / pharmacology*
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Cyclization
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Microbial Sensitivity Tests
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Molecular Structure
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Stereoisomerism
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Terpenes / chemical synthesis*
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Terpenes / chemistry
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Terpenes / pharmacology*
Substances
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7-methyl-7-hydroxy-2,3-benzo(c)octa-1,6-olide
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Antifungal Agents
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Biological Products
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Terpenes