Total synthesis of Englerin A:
| Reference: | Nicolaou, K. C.; Kang, Q.; Ng, S. Y.; Chen, D. Y.-K. J. Am. Chem. Soc. 2010, 132, 8219-8222. DOI |
| Reactions: | Vilsmeier formylation • Aryl-H → Aryl-CHO • O-Bn → O-H • Hydroalumination Alkyne • Pd/H-Alkynyl+Vinyl-X • Si-Alkynyl → H-Alkynyl • Furan synthesis • Mg-Alkyl+Aldehyde • Aldehyde+Mg-R • Pyrone synthesis • Furan oxidation • Cycloaddition Oxopyrilium • Ether-6 • Ether-5 • Bicyclo(321)-oxa • Alkyl-X → Alkyl-SeR • Selenoxide-Ei → Ene • Wacker oxidation • Alkene → Ketone • Aldol-K → Enone • Cyclopentene • Bicyclo(530) • Enone → Allyl-OH • Hydrogenation Alkene • CarboxAmide(Weinreb)+Li-R • Li-Alkyl+CarboxAmide • Baeyer-Villiger • O-H → O-C(O)R • Al-Vinyl → I-Vinyl • CarboxEster → CarboxAmide(Weinreb) • O-C(O)R → O-H • CompE+-CarboxEster/CarboxEster+H2O • Hydrogenation Alkene • Selenide → Selenoxide • |
| Reagents: | AlH2(OR)2-Na+ • AlH2(OR)2-Na+ • I2 • Pd(PPh3)4 • Alkynyl-SiR3 • Carbonate, potassium • AuClPPh3 • POCl3 • DMF (react) • Vilsmeier reagent • Alkyl-MgX • Sulfonyl chloride, methane • NEtiPr2 • Acrylate • H2, Pt • H2, Pd • Selenocyanate, o-nitrophenyl • PBu3 • PdCl2 • CuCl • O2 • KN(SiMe3)2 • BH4-Na+, CeCl3 • Ir(cod)X • Crabtree catalyst • NHMe(OMe) • Alkyl-MgX • Me-Li • Benzoyl chloride, 2,4,6-trichloro • NEt3 • DMAP • Carbonate, potassium • H2, Ir • Perbenzoic acid, 3-chloro • Perbenzoic acid, 3-chloro • Perbenzoic acid, 3-chloro • |