Total synthesis of Lycopladine A:
| Reference: | Staben, S. T.; Kennedy-Smith, J. J.; Huang, D.; Corkey, B. K.; LaLonde, R. L.; Toste, F. D. Angew. Chem. Int. Ed. 2006, 45, 5991-5994 DOI |
| Reactions: | Electrocyclic-6π • Pd/B-Vinyl+Vinyl-X • Alkyne → Alkynyl-I • Sn-Allenyl+Enone • Enone+Sn-R • ConjAdd Sn-R • ConjAdd-Silylation • Carboauration Alkyne • EnolSilane+Carbonium • Cyclopentene • Bicyclo(430) • Pd/B-Alkyl+Vinyl-X • Enone → Enone-α-Halo • Pyridine synthesis • O-Bn → O-H • Alkene isomerization-EZ • |
| Reagents: | NaOMe • I2 • Iodosobenzene-TFA • Pyridine • Vinyl-I • Alkyl-BR2 • PdCl2(dppf) • AsPh3 • Allenyl-SnR3 • SiMe2tBu-OTf • NIS • AgNO3 • Alkynyl-I • AuCl·L • AgBF4 • Vinyl-I • Vinyl-BR2 • Pd/C • DMF (solvent) • Cyclohexadiene • |