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Total synthesis of Neocarzinostatin:
Reference: Myers, A. G.; Glatthar, R.; Hammond, M.; Harrington, P. M.; Kuo, E. Y.; Liang, J.; Schaus, S. E.; Wu, Y.; Xiang, J.-N. J. Am. Chem. Soc. 2002, 124, 5380. DOI
Keywords: Propargyl-OH -> Ynone • Si-Alkynyl -> H-Alkynyl • Ketal -> Diol • O-H -> O-SiPh2tBu • O-SiPh2tBu -> O-H • Si-Alkynyl -> H-Alkynyl • Enal -> Allyl-OH • Alkyl-OH -> Aldehyde-α-OR • O-SiMe2tBu -> O-H • Ketal -> Diol • Diol -> Carbonate • O-H -> O-SiEt3 • O-SiEt3 -> O-H • Li-Alkynyl+Aldehyde • Li/H -> Li-Alkynyl • Wittig-propargyl -> Enyne • Sharpless epoxidation • Sharpless epoxidation • Li-Alkynyl+Ketone • Enone+Li-R • Li/H -> Li-Alkynyl • Si-Alkynyl -> H-Alkynyl • Epoxide -> Allyl-OH • CarboxAcid -> CarboxEster • Dehydration -> Enyne • Li-Alkynyl+Aldehyde • Li/H -> Li-Alkynyl • Felkin-Anh Chelation • Enolsilane+Orthoester • Selenolate+Enone • ConjAdd-Acylation • Selenoxide-Ei -> Enone-5 • Ketone -> Enone • Claisen acylation, formate •
Reagents: Alkynyl-SiR3 • Cr2O7·2PyH (PDC) • PPh3=CH-Alkynyl • Carbonate, potassium • HCl, H2O • DMAP • Hydroperoxide, tbutyl - Ti(OiPr)4 • Epoxide • HF·NEt3 • Propenyl-OR} • LiN(SiMe3)2 • Fluoride, Bu4N+ • AlHiBu2 • Hydroperoxide, tbutyl - Ti(OiPr)4 • Dess-Martin • Chloroacetate • HF·NEt3 • Carbodiimide • TsOH • O=C(Im)2 • Camphor sulfonic acid • NH2Pr • SiEt3-OTf • Martin sulfurane • Epoxide • HF·NEt3 • PPh3, I2 • Imidazole • LiN(SiMe2Ph)2 • Chloride, lithium • SePh-SiMe3 • SiMe3-OTf • Orthoformate • H2O2

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