Total synthesis of Fukinone:
| Reference: | Marshall, J. A.; Cohen, G. M. Tetrahedron Lett 1970, 3865. DOI |
| Reactions: | Allylic oxidation → Enone • ConjAdd Cu-Me • Cu-Me+Enone • Enone+Cu-Me • CompE+-Ketone/CarboxEster+M-R • Wolff-Kishner • Ketone → CH2 • Ketone → EnolCarboxylate • Epoxidation, Peracid • Ketone → Ketone-α-OR • Epoxide rearrangement • Li-Vinyl+Ketone • Ketone+Li-Vinyl • Diol-1,2 → Ketone-α-OR • CompOx-Alkyl-OH/Alkyl-OH+DMSO • Ketone-α-OR → Ketone • Alkyl-OH → Ketone • O-H → O-C(O)R • O-H → O-C(O)R • |
| Reagents: | CrO4Na2 • Acetic anhydride • Me-Cuprate • Hydrazine • Glycol • CrO3, H2SO4 (Jones) • LiCPh3 • Acetic anhydride • Propenyl-Li • DMSO, Py·SO3 (Parikh-Doering) • Acetic anhydride • Ca°/NH3 • |