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Total synthesis of Crinine :
Reference: Pearson, W. H.; Lovering, F. E. J. Org. Chem., 1998, 63, 3607. DOI
Keywords: Alkyl-OH → Aldehyde • O-MOM → O-H • O-H → O-SO2R • Allyl-X → Allyl-OAc • Hydrogenation Lindlar • Li-Alkynyl → Zn-Alkynyl • Pictet-Spengler • Amine-6 • Pd/Zn-Alkynyl+Vinyl-X • Negishi coupling • O-H → O-SiMe2tBu • Li/Sn → Li-Azaallyl • Azaallyl anion Cycloaddition • Amine-5 •
Reagents: SnMe3-CH2-NH2 • BuLi(n) • Carbonate, calcium • DMSO, (COCl)2 (Swern) • Formaldehyde • HCl, H2O • Sulfonic anhydride, methane • Acetate, cesium • Carbonate, potassium • Alkynyl-ZnX • ZnCl2 • Fluoride, R4N+ • LiCH2-N=CR2 • BuLi(n) • LiCH2-N=CR2 • PdCl2(PPh3)2

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