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Total synthesis of Cherylline:
Reference: Hart, D. J.; Cain, P. A.; Evans, D. A. J. Am. Chem. Soc. 1978, 100, 1548.DOI
Keywords: CarboxAmide enolate+Ketone • O-Bn → O-H (phenol) • CarboxAmide → Amine • Amine-6 • Ketene+Amine • Peterson → EnoateAmide • Friedel-Crafts Alkylation • Lactam-6 • ArylO-Me → ArylO-H • Quinone synthesis •
Reagents: Ketene, trimethylsilyl • LiNiPr2 • BF3·OEt2 • H2, Pd • AlH4-Li+ • Thiolate, ethyl • DMF (solvent) • Tl(NO2)3

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