Total synthesis of Trifarienols A, B:
| Reference: | Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 5746. DOI |
| Reactions: | EnolSilane → Ketone enolate • Ketone enolate+Alkyl-X • Propargyl-X+Enolate • Li-Alkynyl+Alkyl-X • Li/H → Li-Alkynyl • CarboxEster → Alkyl-OH • Aldehyde → Alkyl-OH • Takai-Lombardo → Ene • Ketone → C=CH2 • Simmons-Smith • Cyclopropane • Spiro(52) • Alkyne isomerization • Pd-Carboxylation • Hydrogenolysis Cyclopropane • CompE+-Ketone/CarboxEster+M-R • Hg-Vinyl → MeO2C-Vinyl • Aldehyde → Aldehyde-α-OH • Cu-Me+Enone • Alkyne Carbomercuration • Cyclohexanone • Bicyclo(331) • Ketal → Ketone • Ketone → EnolSilane • Alkyl-OH → Aldehyde • Ketone → Ketal • |
| Reagents: | Me-Li • Propargyl-Br • Alkynyl-Li • Glycol • BuLi(n) • NH2(CH2)3NH2 • Me-Cuprate • SiMe3-Cl • PdCl2 • CuCl2 • HOMe (react) • CH2Br2, Zn°, TiCl4 • AlH4-Li+ • CH2I2, Sm • HgCl2 • Dess-Martin • Li°/NH3 • SeO2 • BH4-Na+ • CO • HgCl2 • NH(SiMe3)2 (HMDS) • SiMe3-Cl • MeI • |