Total synthesis of Capnellene (Stille):
| Reference: | Crisp, G. T.; Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 7500 DOI |
| Reactions: | Ketone → EnolTriflate • Nazarov • Cyclopentenone • Bicyclo(330) • ConjReduct-Triflation • Enone ConjReduct • Pd/Sn-Vinyl+Vinyl-X+CO • Stille carbonylative coupling • Enone → Ketone • Hydrogenation Enone • Wittig-methyl • Carbonylation • Nazarov • Cyclopentenone • Bicyclo(330) • Pd/Sn-Vinyl+Vinyl-X+CO • Stille carbonylative coupling • Carbonylation • |
| Reagents: | Tf2O • Pyridine, 2,6-di-tBu • BF3·OEt2 • BH(sBu3)-Li+ • Tf2O • Vinyl-SnR3 • Vinyl-SiR3 • Pd(PPh3)4 • H2, Pd • PPh3=CH2 • CO • BF3·OEt2 • Vinyl-SnR3 • Vinyl-SiR3 • Pd(PPh3)4 • CO • |