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Total synthesis of Fluostatin C:
Reference: Yu, M.; Danishefsky, S. J. J. Am. Chem. Soc. 2008, 130, 2783. DOI
Keywords: O-MOM → O-H • Dehydration → Ene • O-SiiPr3 → O-H • Ketone epimerization • Enone epoxidation, nucleophilic • CompOx-Enone/Alkene+ROOH • Alkene → Diol-1,2 • Epoxide → Chlorohydrin • Diels-Alder, Enone • Allylic oxidation → Enone • Benzene synthesis • Enone → Allyl-OH • Alkyl-OH → Ketone-α-OR • O-H → O-SiiPr3 • Ketal → Enone •
Reagents: NaOMe • BH(Et)3-Li+ • SiiPr3-OTf • TsOH·Py • Hydroperoxide, tbutyl • Triton B • OsO4, NMO • RuO4-Pr4N+, NMO • TsOH • SeO2 • NEtiPr2 • O2 • HF • HCl • Acetone (solvent) • TiCl2(OR)2 • Binaphthol • Chiral catalyst •

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