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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 • O-H -> O-Bn • 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 • ConjAdd-Silylation • Enone+Cu-R • Cu-Alkyl+Enone • C-Si -> C-OH, Alkyl • Allylic oxidation -> Allyl-OH • ConjAdd Enolsilane • Enone+Enolsilane • KeteneAcetal+Enone • Radical cyclization(α-Keto) •
Reagents: CuI • Perbenzoic acid, 3-chloro • Li°/NH3 • Fluoride, Bu4N+ • H2O2, K2CO3 • SiMe2tBu-Cl • CrO3Cl·PyH (PCC) • BHsBu3-Li+ • Acetic acid, trifluoro • SeO2 • DMSO, (COCl)2 • CH2=C(OR)(OSiR'3) • LiClO4 • Acetic acid • CrO3, H2SO4 (Jones) • Oxalyl chloride • NH2Me • Carbonate, potassium • AlH4-Li+ • DMSO, (COCl)2 • H2, Pd • AIBN •

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