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Total synthesis of Trifarienols A, B:
Reference: Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 5746. DOI
Keywords: EnolSilane → Ketone enolate • Ketone → Ketal • Ketone enolate+Alkyl-X • Propargyl-X+Enolate • Li-Alkynyl+Alkyl-X • Li/H → Li-Alkynyl • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Aldehyde → Alkyl-OH • Nozaki-Takai → Ene • Ketone → C=CH2 • Simmons-Smith • Cyclopropane • Alkyne isomerization • Pd-Carboxylation • Hydrogenolysis Cyclopropane • CompE+-Ketone/CarboxEster+CH2(ZnBr)2 • Hg-Vinyl → MeO2C-Vinyl • Aldehyde → Aldehyde-α-OH • Cu-Me+Enone • Alkyne Carbomercuration • Ketal → Ketone • Ketone → EnolSilane •
Reagents: MeLi • Propargyl-Br • Alkynyl-Li • Glycol • BuLi(n) • Propylene diamine • LiCuMe2 • SiMe3-Cl • PdCl2 • CuCl2 • CH2Br2, Zn°, TiCl4 • AlH4-Li+ • CH2I2, Sm • HgCl2 • Dess-Martin • Li°/NH3 • SeO2 • BH4-Na+ • CO • HgCl2 • NH(SiMe3)2 (HMDS) • SiMe3-Cl •

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