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Total synthesis of Tedanolide Macrolactone:
Reference: Hassfeld, J.; Eggert, U.; Kalesse, M. Synthesis 2005, 1183. DOI
Keywords: O-H → O-PMB • EnoateEster → Allyl-OH • Allyl-OH → Enal • CarboxAmide(Evans) → CarboxAmide(Weinreb) • O-H → O-SiMe2tBu • O-H → O-SiEt3 • O-H → O-Me • O-PMB → O-H • Alkyl-OH → Ketone • O-H → O-SiMe2tBu • Ketone → Alkyl-OH • Alkyl-OH → Aldehyde-α-OR • Pinnick oxidation • Aldehyde → CarboxAcid • O-PMB → O-H • Mitsunobu → Lactone-9+ • Alkyl-OH → Alkyl-OC(O)R • Lactone-9+ • B-Allyl-Ipc+Aldehyde • Aldol-B-Ipc • Wittig-carboxymethyl → EnoateEster • Aldol-B-Evans • CarboxAmide(Weinreb) → Aldehyde • CarboxEster enolate+Aldehyde • Ketone enolate+Aldehyde • Aldol-Li → Aldol • Felkin-Anh • Ozonolysis • Mukaiyama Aldol • Aldol-Si • Ketene acetal+Aldehyde • Aldehyde+EnolSilane •
Reagents: Crotyl-B(Ipc)2 • BF3·OEt2 • NaH • O3 • PPh3=C(Me)-CO2R • AlHiBu2 • MnO2 • Chiral auxiliary-Evans • BOTfBu2 • NMe(OMe)-AlMe2 • SiMe2tBu-OTf • AlHiBu2 • SiEt3-OTf • SiMe2tBu-Cl • Me3O+ X- • DDQ • RuO4-Pr4N+, NMO • NaN(SiMe3)2 • SiMe2tBu-OTf • AlHiBu2 • RuO4-Pr4N+, NMO • Chlorite, sodium • DDQ • PPh3, DEAD • AD-Mix • Chiral auxiliary-Boronate • DMSO (solvent) •

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