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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 • Chiral auxiliary-Evans • 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, R4N+ • Me2S •

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