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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-1,2 • 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-1,2 • Diol-1,2 → 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-Silylation • Selenoxide-Ei → Enone • Ketone → Enone • Claisen acylation, formate •
Reagents: Alkynyl-SiR3 • Cr2O7·2PyH (PDC) • PPh3=CH-Alkynyl • Carbonate, potassium • HCl, H2O • DMAP • Hydroperoxide, tbutyl • Epoxide • HF·NEt3 • Propenyl-OR • LiN(SiMe3)2 • Fluoride, R4N+ • AlHiBu2 • Hydroperoxide, tbutyl • Dess-Martin • Chloroacetate • HF·NEt3 • Carbodiimide • TsOH • O=C(Imid)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 • Chloroacetate •

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