Total synthesis of Tedanolide Macrolactone Model:
| Reference: | Hassfeld, J.; Eggert, U.; Kalesse, M. Synthesis 2005, 1183. DOI |
| Reactions: | CarboxAmide(Evans) → CarboxAmide(Weinreb) • O-H → O-SiMe2tBu • Mitsunobu → Lactone-9+ • Alkyl-OH → Alkyl-OC(O)R • Lactone-9+ • B-Allyl-Ipc+Aldehyde • Aldehyde+B-Allyl (asym) • Wittig-carboxymethyl → EnoateEster • Aldol-B-Evans • CarboxAmide enolate+Aldehyde (asym) • CarboxAmide(Weinreb) → Aldehyde • CarboxEster enolate+Aldehyde • Ketone enolate+Aldehyde • Aldol-Li → Aldol • Felkin-Anh • Ozonolysis • Mukaiyama Aldol • Aldol-Si • Ketene acetal+Aldehyde • Aldehyde+EnolSilane • EnoateEster → Allyl-OH • Allyl-OH → Enal • Alkene → Diol-1,2 (asym) • O-H → O-SiMe2tBu • O-PMB → O-H • Pd-Deallylation • CarboxEster → CarboxAcid (allyl) • CarboxEster → CarboxEster • O-PMB → O-H • Alkyl-OH → Ketone • O-H → O-PMB • O-H → O-Me • O-H → O-SiMe2tBu • O-H → O-SiEt3 • |
| Reagents: | Crotyl-B(Ipc)2 • BF3·OEt2 • NaH • O3; PPh3 • PPh3=C(Me)-CO2R • AlHiBu2 • MnO2 • Chiral auxiliary (amide-Evans) • B(OTf)Bu2 • NMe(OMe)-AlMe2 • SiMe2tBu-OTf • AlHiBu2 • Butadiene, 1-OR • SiEt3-OTf • SiMe2tBu-Cl • Me3O+ X- • DDQ • RuO4-Pr4N+, NMO • NaN(SiMe3)2 • SiMe2tBu-OTf • DDQ • PdCl2(PPh3)2 • PPh3, DEAD • AD-Mix • Chiral auxiliary (boronate) • Chiral auxiliary (amide-Evans) • DMSO (solvent) • HSnBu3 • |