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Total synthesis of Dihydroiso-Codeine:
Reference: Parker, K. A.; Fokas, D. J. Am. Chem. Soc. 1992, 114, 9688
Keywords: N-H -> N-SO2R --- Luche reduction --- Enone -> Allyl-OH --- N-H -> N-Me --- Epoxide -> Allyl-OH --- O-H -> O-SiMe2tBu --- Mitsunobu -> Ether --- Alkyl-OH -> Alkyl-OR(2°) --- Ether-5 --- O-SiMe2tBu -> O-H --- Alkyl-OH -> Ketone-α-OR --- Radical cyclization(Aryl) --- ConjAdd Amine --- Amine-6 --- Birch reduction --- Epoxidation, peracid
Reagents: Li°/NH3 --- TsCl, NEt3 --- BH4-Na+, CeCl3 --- Carbonate, potassium --- Perbenzoic acid, 3-chloro --- Ti(OiPr)4 --- SiMe2tBu-OTf --- PBu3, DEAD --- HSnBu3 --- AIBN --- HF --- Li° --- DMSO, (COCl)2

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