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Total synthesis of Ptilocaulin:
Reference: Roush, W. R.; Watts, A. E. J. Am. Chem. Soc. 1984, 106, 721. DOI
Keywords: Hydroboration Alkene • Aldehyde -> Nitrone • Nitrone synthesis • N-OR -> N-H • Alkyl-OH -> Ketone • CompOx-Alkyl-OH/Amine+CrO3 • N-Bn -> N-H • Retro-Aldol • Ketone -> Ketone-α-SR • Sulfide -> Sulfoxide • KetoSulfoxide dianion+Alkyl-X • Sulfoxide-Ei -> Enone • Si-Allyl+Enone • Enone+Si-R • ConjAdd Si-Allyl • Ketone -> Enolphosphate • Hydroboration Alkene • Ketone -> Alkene • Alkyl-OH -> Aldehyde • Nitrone Cycloaddition • Guanidine synthesis •
Reagents: LiNiPr2 • Disulfide, phenyl • Perbenzoic acid, 3-chloro • LiNiPr2 • Carbonate, calcium • TiCl4 • LiNiPr2 • P(O)(OR)2Cl • BH-BBN • H2O2 • Li°/EtNH2 • CrO3Cl·PyH (PCC) • Zn° • HCl • CrO3, H2SO4 (Jones) • H2, Pd •

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