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Total synthesis of Dihydro-Codeine:
Reference: Parker, K. A.; Fokas, D. J. Am. Chem. Soc. 1992, 114, 9688; DOI J. Org. Chem. 2006, 71, 449. DOI
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 • Alkyl-OH → Ketone-α-OR • ConjAdd Amine • Amine-6 • Birch reduction • Epoxidation, peracid • Henbest • Ether-5 • HWE → EneSulfide • O-SiMe2tBu → O-H • Radical cyclization(Aminyl) • Radical cyclization(Aryl) •
Reagents: Li°/NH3 • TsCl, NEt3 • BH4-Na+, CeCl3 • Carbonate, potassium • Perbenzoic acid, 3-chloro • Ti(OiPr)4 • SiMe2tBu-OTf • PBu3, DEAD • Li°/NH3 • DMSO, (COCl)2 (Swern) • HSnBu3 • AIBN • P(O)(OR)2CH2-SR • BuLi(n) • HF • NEt3

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