Total synthesis of SNF4435 C/D:
| Reference: | Beaudry, S. M.; Trauner, D. Org. Lett. 2005, 7, 4475-4477. DOI |
| Reactions: | CarboxEster → Ketene acetal • CarboxEster → CarboxEster-α-Br • Ether-5 • O-H → O-Alkyl • Electrocyclic-8π • Spiro(74) • Electrocyclic-6π • Bicyclo(420) • Pd/Sn-Vinyl+Vinyl-X • KetoEster dianion+Acyl-X • Li-Vinyl+Aldehyde • Enal+Li-R • Claisen-Ireland • Pd-Stannylation • Vinyl-I → Vinyl-Sn • CarboxEster → CarboxEster-α-OR • Ether-5 • CompE+-Aldehyde/Vinyl-X+M-R • Pyrone synthesis • Enol → EnolEther • CarboxEster → CarboxAcid • CarboxAcid → CarboxAmide • Williamson esterification • CarboxAcid → CarboxEster • O-H → O-SiMe2tBu • CompNu-O-H/O-H+R3Si-X • O-H → O-C(O)R • |
| Reagents: | SnMe3-SnMe3 • PdCl2(MeCN)2 • Vinyl-SnR3 • Fluoride, cesium • Vinyl-I • Vinyl-Li • SiMe2tBu-Cl • Acetic anhydride • LiNiPr2 • SiMe3-Cl • Carbonate, potassium • LiNiPr2 • NBS • DMF (solvent) • Acetoacetate • BuLi(n) • DBU • MeOSO2F • SiMe3-Cl • Vinyl-SnR3 • O=C(Imid)2 • Hydroxide, sodium • Acyl imidazole • |