image

Total synthesis of Hinesol:
Reference: Chass, D. A.; Buddhasukh, D.; Magnus, P. D. J. Org. Chem. 1978, 43, 1750. DOI
Keywords: Reformatsky • CarboxEster enolate+Ketone • Ether-5 • CarboxEster → Alkyl-OH • O-H → O-SO2R • Nitrile → CarboxAcid • Fischer esterification • CarboxAcid → CarboxEster • CarboxEster → CarboxEster-α-SeR • CarboxEster → Alkyl-OH • O-H → O-SO2R • Ketal → Diol-1,3 • O-H → O-SO2R • Alkyl-OH → Ketone • Alkyl-SO2R → Alkyl-H • Selenoxide-Ei → EnoateEster • CarboxEster → EnoateEster • Cu-Me+EnoateEster • ConjAdd Cu-R • Ketone+Mg-Alkyl • Mg-Alkyl+Ketone • Li-Sulfone+Alkyl-X • Alkyl-X+Li-R • Epoxide reduction • Wagner-Meerwein • Mechanism • Alkyl-X → Alkyl-CN • Dehydration → Ene • Epoxidation, peracid • Diol-1,3 → Ketal • Grob fragmentation • Mechanism • Li-Sulfone+Ketone • Barton remote functionalization •
Reagents: Bromoacetate • Bromoacetate • Zn° • HgO • AlH4-Li+ • TsCl, Py • Cyanide, sodium • Hydroxide, sodium • BF3·OEt2 • LiNiPr2 • Periodate, sodium • LiCuMe2 • H2SO4 • Acetone (react) • AlH4-Li+ • TsCl, Py • LiCH2-Sulfonyl • TsCl, Py • CrO3·Py2 (Collins) • Al(Hg) • MeMgI • Perbenzoic acid, 3-chloro • Bicarbonate, sodium • AlH4-Li+ • Burgess reagent • Diselenide, phenyl • Acetic anhydride • Photochemistry • DMSO (solvent) • DMSO (solvent) • CuSO4 • NaH • LiCHR-Sulfonyl • DMSO (solvent) •

Syntheses Home