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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, 7423-7424. 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+CarboxEster • CarboxEster+Li-R • Kowalski reaction • O-MOM → O-H • Alkyl-OH → Aldehyde • ArylO-Me → ArylO-H • Danheiser benzannulation • CarboxAmide enolate(Evans)+Alkyl-X • Alkyl-X+Enolate • Li-Alkyl+Ketone • Enone-β-OR+Li-R • Stork-Danheiser • Wittig-methyl • RCM → Ring-C • Ynol-OSi • ArylO-H → ArylO-R • Benzene synthesis • Lemieux-Johnson oxidation • Alkyl-OH → Alkyl-I • Hydrogenation alkene • Li/I → Li-Alkyl • Mechanism • Myers reductive coupling • Li-Alkyl+Imine • Hydrazone+Li-R •
Reagents: NaN(SiMe3)2 • H2O2, LiOH • Carbonate, potassium • CH2Br2 • BuLi(n) • CH2Br2 • BuLi(n) • AlH4-Li+ • Cl-CH2-OR • H2, Pd • PPh3, I2 • Alkyl-Li • BuLi(tert) • Fluoride, R4N+ • Carbonate, potassium • HCl, H2O • PPh3, I2 • OsO4, NaIO4 • Hydrazine, tosyl • LiCHBr2 • LiCHBr2 • HCl, MeOH • Dess-Martin • PPh3=CH2 • H2, Pd • B(Br)3 • Allyl-Br • Grubbs I • SiiPr3-OTf • SiMe2tBu-OTf • Imidazole • BuLi(tert) • LiTMP • LiTMP •

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