Total synthesis of Cherylline:
| Reference: | Hart, D. J.; Cain, P. A.; Evans, D. A. J. Am. Chem. Soc. 1978, 100, 1548.DOI |
| Reactions: | CarboxAmide enolate+Ketone • Ketene+Amine • Peterson → EnoateAmide • Li-Silane+Ketone • Enone+Li-R • Friedel-Crafts Alkylation • Lactam-6 • O-Me → O-H (phenol) • Quinone synthesis • O-Bn → O-H (phenol) • N-C(O)R → N-CH2R • Amine-6 • |
| Reagents: | Ketene, trimethylsilyl • LiNiPr2 • BF3·OEt2 • H2, Pd • AlH4-Li+ • Thiolate, ethyl • DMF (solvent) • Tl(NO2)3 • HOMe (react) • |