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- W2023256602 abstract "An enantioselective synthesis of platensimycin, a novel antibiotic natural product that inhibits bacterial β-ketoacyl-(acyl-carrier-protein) synthase (FabF), is described. Our synthetic strategy for the construction of the oxatetracyclic core involved an intramolecular Diels−Alder reaction. Our preliminary studies provided a complex tetracyclic product by first undergoing an interesting 1,5-hydride shift followed by a Diels−Alder reaction. Further optimization of the diene’s electronic properties, by incorporation of a methoxy group, led to the oxatetracyclic core of platensimycin. The three required chiral centers, including two all-carbon quaternary chiral centers, were built in the intramolecular Diels−Alder step. The synthesis utilized natural (+)-carvone as the key chiral starting material, which determined the stereochemistry of the final product. The synthesis also featured an efficient Petasis olefination, a hydroboration sequence, a Gais’s asymmetric Horner−Wadsworth−Emmons reaction, and a mercury salt catalyzed enol ether isomerization." @default.
- W2023256602 created "2016-06-24" @default.
- W2023256602 creator A5041773055 @default.
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- W2023256602 date "2009-01-05" @default.
- W2023256602 modified "2023-10-05" @default.
- W2023256602 title "Total Synthesis of (−)-Platensimycin, a Novel Antibacterial Agent" @default.
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- W2023256602 doi "https://doi.org/10.1021/jo802261f" @default.
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