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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 • Alkyl-X+Enolate • Sulfoxide-Ei → Enone • Si-Allyl+Enone • Enone+Si-R • ConjAdd Si-Allyl • Ketone → Enolphosphate • Hydroboration Alkene • Ketone → Alkene • EnolPhosphate → Vinyl-H • 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) • NBn(OH)H • Zn° • HCl • CrO3, H2SO4 (Jones) • H2, Pd •

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