Total synthesis of Fluostatin C:
| Reference: | Yu, M.; Danishefsky, S. J. J. Am. Chem. Soc. 2008, 130, 2783. DOI |
| Reactions: | O-MOM → O-H • O-SiiPr3 → O-H • Ketone epimerization • Enone epoxidation, nucleophilic • CompOx-Enone/Alkene+ROOH • Alkene → Diol-1,2 • Epoxide → Chlorohydrin • Diels-Alder, Enone • Bicyclo(440) • Bicyclo(430) • Allylic oxidation → Enone • Benzene synthesis • Enone → Allyl-OH • Diol-1,2 → Ketone-α-OR • O-H → O-SiiPr3 • Ketal → Enone • Dehydration → 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, H2O • Acetone (solvent) • TiCl2(OR)2 • Binaphthol • Chiral catalyst (diol) • |