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Total synthesis of Dihydro-Codeine:
Reference: Parker, K. A.; Fokas, D.J. Org. Chem. 2006, 71, 449. DOI
Keywords: N-H -> N-SO2R • Luche reduction • Enone -> Allyl-OH • Henbest • Mitsunobu -> Ether • Allyl-OH -> Allyl-OAr(2°) • Radical cyclization(Aryl) • Ether-5 • N-SO2R -> N-H • Alkyl-OH -> Ketone-α-OR • Radical cyclization(Aminyl) • Amine-6 • Epoxide -> Allyl-OH • Epoxidation, peracid • N-H -> N-Me • Birch reduction •
Reagents: Li°/NH3 • TsCl, NEt3 • Carbonate, potassium • BH4-Na+, CeCl3 • Perbenzoic acid, 3-chloro • Ti(OiPr)4 • PPh3, DEAD • SiMe2tBu-OTf • HF • HSnBu3 • Li°/NH3 • DMSO, (COCl)2 • NEt3 • AIBN • NEtiPr2

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