image

Total synthesis of Fluostatin C:
Reference: Yu, M.; Danishefsky, S. J. J. Am. Chem. Soc. 2008, 130, 2783. DOI
Keywords: Enone -> Allyl-OH • O-H -> O-SiiPr3 • Ketal -> Enone • Alkyl-OH -> Ketone-α-OR • O-MOM -> O-H • Dehydration -> Ene • Allylic oxidation -> Enone • Enone-6 -> Phenol • O-SiiPr3 -> O-H • Ketone epimerization • Epoxidation, nucleophilic Enone • Alkene -> Diol-1,2 • Epoxide -> Chlorohydrin • Diels-Alder, Enone •
Reagents: NaOMe • BHEt3-Li+ • SiiPr3-OTf • TsOH·Py • Hydroperoxide, tbutyl • Triton B • OsO4, NMO • RuO4-Pr4N+, NMO • TsOH • SeO2 • NEtiPr2 • HF • HCl • Acetone (solvent) • TiCl2(OR)2 • Binaphthol • Chiral catalyst •

Syntheses Home