Total synthesis of Pinguisone:
| Reference: | Bernasconi, S.; Gariboldi, P.; Jommi, G.; Sisti, M.; J. C. S., Perk. Trans. I 1981, 2394. DOI |
| Reactions: | Sulfoxide-Ei → Enone • Ketone → Enone • Cu-Me+Enone • ConjAdd Cu-Me • Furan synthesis • ConjAdd M-SR • Enone+Thiolate • CompE+-Enone/Enone+M-SR • CompE+-Acyl-X/Alkyl-X+Enolate • CompRed-Enone/Ketone+M-H • Cu-Me+Enone • ConjAdd-Acylation • Claisen acylation, acyl-X • Ketone enolate+CarboxCl • CarboxCl+Enolate • Cyclopentenone • Ether-5 • Sulfide → Sulfoxide • |
| Reagents: | Thiol, propyl • Periodate, sodium • Carbonate, calcium • Me-Cuprate • Me-Cuprate • Chloroacetate • BH-BBN • |