The metabolite thiocarboxylic A () and three close analogues were synthesized in 14 steps. The stereogenic elements were installed via stereoselective Sharpless epoxidation, ()-selective reduction of a dibromide, and a Suzuki cross coupling. Thiocarboxylic A () was obtained in 6% overall yield. The synthetic product and the natural isolate differed markedly in their specific rotations and antibiotic activities against and . This modular synthetic route should be flexible enough to allow the synthesis of other natural and non-natural 3-methoxycarbonyldihydrofuran-4-ones for biological studies.
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| http://dx.doi.org/10.1021/acs.jnatprod.2c00870 | DOI Listing |
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