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Total synthesis of Linoxepin:
Reference: Weinstabl, H.; Suhartono, M.; Qureshi, Z.; Lautens M. Angew.Chem.Int.Ed 2013, 52, 5305–5308. DOI
Keywords: O-H → O-Alkyl • Williamson etherification • Catellani • Pd-Heck coupling • Aldol-Ti → Enone • Pd-Heck coupling • O-H → O-SO2R • Malonic Ester Synthesis • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Epoxide+Enolate • Cyclopropane opening • Decarboxylation • Finkelstein reaction • Alkyl-X → Alkyl-I • Li/H → Li-Aryl • Benzyl-OH → Benzyl-I • Li-Aryl+Carboxamide • O-H → O-THP • Li/H → Li-Aryl • Li-Aryl → I-Aryl • Alkene → Diol-1,2 •
Reagents: HCl • AlCl3 • TsOH • Iodide, sodium • LiNiPr2 • DMF (solvent) • BH4-Na+ • SiMe3-Cl • Iodide, sodium • DHP • TsOH·Py • BuLi(n) • I2 • Carbonate, potassium • Pd(OAc)2 • PPh3 • Carbonate, cesium • SO2 • NEt3 • OsO4, NaIO4 • Chloride, R4N+ • TiCl4 • NEt3 • PdCl2 • PPh3 • Acetate, cesium •

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