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 |
| Reactions: | N-H → N-SO2R • Epoxide → Allyl-OH • O-H → O-SiMe2tBu • CompNu-O-H/O-H+R3Si-X • CompOx-Alkyl-OH/Amine+DMSO • ConjAdd Amine • Amine-6 • Bicyclo(331)-aza • Birch reduction • Epoxidation, peracid • Henbest • Ether-5 • HWE → EneSulfide • O-SiMe2tBu → O-H • Radical cyclization(Aminyl) • Radical cyclization(Aryl) • Cyclohexene • Ether-5 • Bicyclo(440) • Enone → Allyl-OH • Luche reduction • N-H → N-Me • Diol-1,2 → Ketone-α-OR • Mitsunobu → OR • Alkyl-OH → Alkyl-OR • |
| Reagents: | Li°/NH3 • TsCl, NEt3 • BH4-Na+, CeCl3 • Carbonate, potassium • Ti(OiPr)4 • SiMe2tBu-OTf • PBu3, DEAD • Li°/NH3 • DMSO, (COCl)2 (Swern) • HSnBu3 • AIBN • P(O)(OR)2CH2-SR' • BuLi(n) • HF • Perbenzoic acid, 3-chloro • |