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Total synthesis of Gephyrotoxin:
Reference: Chu, S.; Wallace, S.; Smith, M. D. Agew. Chem. Int. Ed. 2014, 53, 13826 –13829. DOI
Keywords: O-H → O-SiMe2tBu • N-H → N-Boc • Wittig-methoxymethyl • EnolEther → Aldehyde • Aldehyde → Alkyl-OH • Mg-Alkyl+CarboxAmide • Ozonolysis • Wittig-ketomethyl → Enone • ConjAdd Enamine • Enone+Enamine • Ketone → Enamine • EnolPhosphate → Alkyne • Ketone → EnolPhosphate • Alkyne → In-Vinyl • Pd/In-Vinyl+Alkynyll-I • Alkyl-OH → Aldehyde • Si-Alkynyl → H-Alkynyl • Iminium → Amine •
Reagents: KN(SiMe3)2 • Alkynyl-I • Boc2O • BF3·OEt2 • BH(sBu3)-Li+ • KN(SiMe3)2 • O3 • PPh3 • Acetic acid, trifluoro • BH(OAc)3-Na+ • NEt3 • LiTMP • P(O)(OEt)2Cl • LiTMP • HCl • BH4-Na+ • InHCl2 • BEt3 • Acetic acid • Pd2(dba)3 • Carbonate, potassium • DMSO, (COCl)2 (Swern) • PPh3=CH-OMe • DMAP •

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