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Total synthesis of Crinine:
Reference: Martin, S. F.; Campbell, C. L. J. Org. Chem. 1988, 53, 3184 DOI
Keywords: Ketal → Ketone • Ketone → Ketone-α-Halo • Ketone-α-Halo → Enone • N-Allyl → N-H • Amine-5 • Enone → Allyl-OH • O-H → O-SO2R • Allyl-X → Allyl-OAc • O-C(O)R → O-H • Aldol-enamine → Enone • Pictet-Spengler • N-Bn → N-H • Aldehyde azaenolate+Alkyl-X • Alkyl-X+Azaenolate • HWE → Enamine •
Reagents: Pyrrolidine • Tribromide, ammonium • DBU • Pd(PPh3)4 • AlH3 • SO2 • NEt3 • Acetate, cesium • Carbonate, potassium • Formaldehyde • O=C(OR)Cl • HCl, H2O • P(O)(OR)2CH2-NR2 • BuLi(n) • Bromoethylamine •

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