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Total synthesis of SNF4435 C/D:
Reference: Beaudry, S. M.; Trauner, D. Org. Lett. 2005, 7, 4475-4477. DOI
Keywords: O-H → O-SiMe2tBu • O-H → O-C(O)R • Ether-5 • Electrocyclic-8π • Electrocyclic-6π • Pd/Sn-Vinyl+Vinyl-X • Stille coupling • Ketoester dianion+Acyl-X • Acyl-Imidazole+Enolate • Li-Vinyl+Aldehyde • Enal+Li-R • Claisen-Ireland • Pd-Stannylation • Vinyl-I → Vinyl-Sn • CarboxEster → CarboxEster-α-OH • CompE+-Aldehyde/Vinyl-X+Li-R • CarboxAcid → CarboxAmide • CarboxEster → CarboxAcid •
Reagents: SnMe3-SnMe3 • PdCl2(MeCN)2 • Vinyl-SnR3 • Fluoride, cesium • Vinyl-Li • SiMe2tBu-Cl • Acetic anhydride • LiNiPr2 • SiMe3-Cl • Carbonate, potassium • LiNiPr2 • NBS • DMF (solvent) • BuLi(n) • DBU • MeOSO2F • SiMe3-Cl • Vinyl-SnR3 • O=C(Imid)2 • Hydroxide, sodium •

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