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Total synthesis of Hexacyclinic Acid (A,B,C-Rings):
Reference: Stellfeld, T.; Bhatt, U.; Kalesse, M. Org. Lett. 2004, 6, 3889. DOI
Keywords: O-H -> O-SiMe2tBu • EnoateEster -> Allyl-OH • Allyl-OH -> Enal • CarboxAmide(Evans) -> CarboxAmide(Weinreb) • Propargyl-OH -> Ynone • O-H -> O-SiMe2tBu • CarboxAmide(Weinreb) -> Aldehyde • Ketone -> Alkyl-OH • O-H -> O-SiPh2tBu • Alkyl-OH -> Ketone • HWE -> DienoateEster • Aldol-B-Evans • Diels-Alder, Intram, Ynone • Olefin cross metathesis • Enolsilane+EnoateEster • ConjAdd Enolsilane • Mg-Alkynyl+Aldehyde • Cu-Vinyl+Enone • Ozonolysis •
Reagents: SiMe2tBu-Cl • O3 • P(O)(OR)2CH2-Vinyl • LiNiPr2 • AlHiBu2 • MnO2 • BOTfBu2 • NMe(OMe)-AlMe2 • Alkynyl-MgX • Dess-Martin • SiMe2tBu-OTf • AlHiBu2 • Vinyl-MgX • CuBr·SMe2 • AlH4-Li+ • Grubbs-Hoveyda • Acrylate • SiPh2tBu-Cl • Camphor sulfonic acid • RuO4-Pr4N+, NMO • SiMe3-I • Fluoride, Bu4N+ • Me2S •

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