Total synthesis of Mitrephorone A New:
| Reference: | Richter, M. J. R.; Schneider, M.; Brandstätter, M.; Krautwald, M.; Carreira, E. M. J. Am. Chem. Soc. 2018, 140, 16704-16710. DOI |
| Reactions: | Claisen acylation, Mander • Ketone enolate+Mander • Mander+enolate • Diels-Alder, Enal (asym) • Wittig-methyl • EnolSilane → Ketone • Dehydroamination → Enone • Diels-Alder, Intram, Ene • Cyclopropane • Bicyclo(222) • CarboxEster → Alkyl-OH • EnolSilane → Ketone • O-H → O-SO2Me • Alkyl-X → Alkyl-CN • Cyanide+Alkyl-X • Li-Vinyl+Ketone • CompE+-Ketone/Nitrile+M-R • Li/Sn → Li-Vinyl • Li-R → La-R • O-H → O-SiEt3 • Li-Alkynyl+Aldehyde • Nitrile → Aldehyde • Propargyl-OH → Ynone • Diels-Alder, Intram, Yne • Bicyclo(440) • Cu-Me+Enone-β-X • ConjAdd-Elimination • Enone-β-X+Cu-R • ConjAdd Cu-Me • Hydrogenation Alkene • ConjAdd M-CN • Nitrile → CarboxAmide • CarboxAmide → CarboxAcid • Ketone → Ketone-1,2-di • Ketone-1,2-di • O-SiEt3 → O-H • Ketone → Ketone-a-OR • Ether-4 • Bicyclo(420)-oxa • Bicyclo(311)-oxa • Ketone → EnolSilane • CarboxAcid → CarboxEster • |
| Reagents: | Butadiene, 2-OR • Butadiene, 1-NR2 • Chiral catalyst (diol) • PPh3=CH2 • HCl, H2O • LiNiPr2 • O=C(OR)CN • SiMe2tBu-OTf • Butadiene, 2-OR • LiN(SiMe3)2 • AlHiBu2 • HCl, H2O • Sulfonyl chloride, methane, NEt3 • Cyanide, potassium • DMSO (solvent) • Vinyl-SnR3 • BuLi(n) • Vinyl-Li • LaCl3 • SiEt3-Cl • DMF (solvent) • AlHiBu2 • LiNiPr2 • Dess-Martin • Me-Cuprate • H2, Pt • Hydroxide, potassium • Diazomethane, silyl • SeO2 • TASF • DMF (solvent) • Butadiene, 1-NR2 • |