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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-OH -> Allyl-OAc • Hydrogenation Lindlar • Pictet-Spengler • Amine-6 • Allyl-OSO2R -> Allyl-OAc • Alcohol inversion • 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 • Formaldehyde • HCl • MeSO2-O-SO2Me • Acetate, cesium • Carbonate, potassium • Alkynyl-ZnX • ZnCl2 • Fluoride, Bu4N+ • LiCH2-N=CR2 • BuLi(n) • LiCH2-N=CR2

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