Total synthesis of Tamiflu:
| Reference: | Ishikawa, H.; Suzuki, T.; Hayashi, Y. Ang. Chem. Int. Ed. 2009, 48, 1307 DOI |
| Reactions: | ConjAdd EnAmine • EneNitro+EnAmine (asym) • EnAmine+EneNitro (asym) • ConjAdd Nitronate • Nitronate+EnoateEster • HWE → EnoateEster (intram) • Cyclohexene • CarboxAcid → CarboxCl • CarboxCl → CarboxAzide • Curtius • C-CO2H → C-N • Nitro → Amine • Dehydrosulfenylation → EnoateEster • CarboxEster → CarboxAcid (tBu) • ConjAdd M-SR • EnoateEster+Thiolate • |
| Reagents: | Pyrrolidine • Chloroacetate • EnePhosphonate • Carbonate, cesium • P(O)(OR)2CH2-C(O)OR' • Thiol, tolyl • Acetic acid, trifluoro • Oxalyl chloride • DMF (solvent) • Azide, sodium • Acetic anhydride • SiMe3-Cl • NH3 • Carbonate, potassium • |