Total synthesis of Lucilactaene:
| Reference: | Coleman, R. S.; Walczak, M. C.; Campbell, E. L. J. Am. Chem. Soc. 2006, 127, 16038. DOI |
| Reactions: | O-SiEt3 → O-H • N-SEM → N-H • Vinyl-Br → Vinyl-I • Pd/Sn-Vinyl+Vinyl-X • CompNu-Sn-Vinyl/B-Vinyl+R-I • Pd/Mg-Alkynyl+Vinyl-X • Alkyne Hydrosilylation • Cu-SiR3+Alkyne • Allyl-OH → EnoateEster • Ozonolysis • CompOx-Alkene/EnoateAmide+O3 • In-Allyl+CarboxAmide • Si-Vinyl → I-Vinyl • Pd/B-Vinyl+Vinyl-X • O-H → O-SiEt3 • Cu-Vinyl+CarboxCl • CarboxCl+Cu-R • Vinyl-I → Vinyl-Mg • Mg-R → Cu-R • ConjAdd M-OR • Ether-5 • Alkyne Hydrostannation • Sn-Vinyl → I-Vinyl • |
| Reagents: | HSnBu3 • I2 • Vinyl-I • Alkynyl-MgX • Pd(PPh3)4 • CuCN • Vinyl-SiR3 • MnO2 • HOMe (react) • NIS • Vinyl-I • Iodide, sodium • Vinyl-I • Allyl-In • DMF (solvent) • O3 • BH4-Na+ • SiEt3-OTf • Alkyl-MgX • CuCN • Acryloyl-Cl • Vinyl-Br • Vinyl-Br • Vinyl-BR2 • Vinyl-SnR3 • Pd2(dba)3 • AsPh3 • Vinyl-BR2 • Pd(OAc)2 • Carbonate, sodium • Acetic acid, trifluoro • AIBN • |