image

Total synthesis of Paniculatine:
Reference: Sha, C.-K.; Lee, F.-K.; Chang, C.-J. J. Am. Chem. Soc 1999, 121, 9875. DOI
Keywords: EnolSilane → Ketone-α-Halo • Ketone → Alkyl-OH • Si-Aryl → H-Aryl • O-H → O-SiMe2tBu • Alkyl-OH → Ketone • Ketone → Alkyl-OH • Si-Vinyl → H-Vinyl • Allyl-OH → Enone • O-SiMe2tBu → O-H • Alkyl-OH → CarboxAcid • CarboxAcid → CarboxCl • CarboxAcid → CarboxAmide • CarboxEster → CarboxAmide • CarboxAmide → Amine • Amine-6 • Alkyl-OH → Ketone • O-Bn → O-H • CompRed-Benzyl-X/Ketone+H2 • ConjAdd-Silylation • Enone+Cu-R • Cu-Alkyl+Enone • ConjAdd Cu-R • Si-Alkyl → HO-Alkyl • Allylic oxidation → Allyl-OH • ConjAdd EnolSilane • Enone+EnolSilane • KeteneAcetal+Enone • Radical cyclization(α-Keto) • O-H → O-Bn •
Reagents: CuI • Perbenzoic acid, 3-chloro • Li°/NH3 • Fluoride, R4N+ • H2O2, K2CO3 • SiMe2tBu-Cl • CrO3Cl·PyH (PCC) • BH(sBu3)-Li+ • Benzyl-X • Acetic acid, trifluoro • SeO2 • DMSO, (COCl)2 (Swern) • Ketene acetal • LiClO4 • Acetic acid • CrO3, H2SO4 (Jones) • Oxalyl chloride • NH2Me • Carbonate, potassium • AlH4-Li+ • DMSO, (COCl)2 (Swern) • H2, Pd • HSnBu3 • AIBN •

Syntheses Home