Total synthesis of Isocyano-epi-Amphilectene:
| Reference: | Pronin, S. V.; Shenvi, R. A. J. Am. Chem. Soc. 2012, 134, 19604–19606. DOI |
| Reactions: | Enone → Enone-α-Halo • Pd/Zn-Vinyl+Vinyl-X • Mg-R → Zn-R • Ketone → EnolSilane • Diels-Alder, Enone • Diels-Alder, Intram, Ene • Bicyclo(440) • Dehydroalkoxylation → Enone • Decarboxylation Krapcho • ConjAdd Cu-Vinyl • Cu-Vinyl+Enone • Mg-R → Cu-R • Mg-Alkyl+Ketone • Ketone protection enolate • Li-Silane+Ketone • Li-R → Ce-R • O-H → O-C(O)R • Peterson → Ene • Alkyl-OH → Alkyl-NC(3°) • |
| Reagents: | I2 • Vinyl-MgX • ZnBr2 • Pd(PtBu3)2 • NEt3 • SiMe2tBu-OTf • Yb(OTf)3 • Iodide, lithium • Vinyl-MgX • CuBr·SMe2 • Me-MgBr • LiCH2-SiR3 • CeCl3 • Cyanide, trimethylsilyl • Butadiene, 1-OR • Butadiene, 2-OR • Lutidine • Pyridine • |