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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+Me-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 -> Vinyl-CO2Me • Aldehyde -> Aldehyde-α-OH • Cu-Me+Enone • Alkyne Carbomercuration •
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

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