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Total synthesis of Cylindrocyclophane F:
Reference: Smith, A. B.; Kozmin, S. A.; Paone, D. V J. Am. Chem. Soc. 1999, 121, 7423. DOI
Keywords: CarboxAmide(Evans) -> CarboxEster --- Williamson esterification --- CarboxEster -> Alkyl-OH --- O-H -> O-MOM --- O-Bn -> O-H --- Li/I -> Li-Alkyl --- Alkene cleavage --- Li-Dibromomethyl+Ketone --- Kowalski reaction --- Li-Dibromomethyl+Ketone --- Kowalski reaction --- O-MOM -> O-H --- Alkyl-OH -> Aldehyde --- Aryl-OMe -> Aryl-OH --- Danheiser benzannulation --- Li/I -> Li-Alkyl --- Amide enolate(Evans)+Allyl-X --- Li-Alkyl+Enone --- Enone-β-OR+Li-Alkyl --- Stork-Danheiser --- Wittig-methyl --- RCM -> Ring-C --- Ynol-OSi --- Aryl-OH -> Aryl-OMe --- Benzene synthesis --- Mechanism --- Lemieux-Johnson oxidation --- Alkyl-OH -> Alkyl-I --- Hydrogenation-Ene
Reagents: NaN(SiMe3)2 --- H2O2, LiOH --- Carbonate, potassium --- CH2Br2, LiTMP --- BuLi(n) --- CH2Br2, LiTMP --- BuLi(n) --- AlH4-Li+ --- Cl-CH2-OR --- H2, Pd --- PPh3, I2 --- Alkyl-Li --- BuLi(tert) --- Fluoride, Bu4N+ --- Carbonate, potassium --- HCl --- I2 --- OsO4, NaIO4 --- Hydrazine, tosyl --- BuLi(tert) --- HCl, MeOH --- Dess-Martin --- Ph3P=CH2 --- Pd/C --- BBr3 --- Allyl-Br --- Grubbs I --- SiiPr3-OTf --- SiMe2tBu-OTf --- Imidazole

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