Total synthesis of Vetispirene:
| Reference: | Paquette, L. A.; Yan, T. H. Tetrahedron Lett. 1982, 23, 3227. DOI |
| Reactions: | O-H → O-Me • McMurry coupling → Ene • 1,3-Sigmatropic • Cyclopentene • Spiro(54) • Simmons-Smith • Cyclopropane • Dehydroalkoxylation → Diene • Si-Allyl+Ketone • Ketone+Si-R • Vinyl-H → Vinyl-Br • Li/Br → Li-Vinyl • Alkyl-OH → Aldehyde • Mg-Alkyl+Silane • Li-Vinyl+Aldehyde • |
| Reagents: | CH2I2, ZnEt2 • MnO2 • BuLi(n) • TsOH • Br2 • Me-MgI • BuLi(n) • Formaldehyde • HMPA (solvent) • TiCl3 • Fluoride, R4N+ • Acetone (react) • Vinyl-Br • Vinyl-SiR3 • |