Total synthesis of Retronecine (Vedejs):
| Reference: | Vedejs, E.; Larsen, S.; West, F. G. J. Org. Chem. 1985, 50, 2170–2174. DOI |
| Reactions: | N-H → N-Alkyl • Lactam → Lactam-α-OR • O-H → O-Bn • CarboxAmide → Imidate • Azomethine ylide Cycloaddition • Bicyclo(330)-aza • Dehydroalkoxylation → EnoateEster • ConjReduct-Selenation • Selenide → Selenoxide • Selenoxide-Ei → EnoateEster • CarboxEster → Alkyl-OH • N-Bn → N-H • Photochemistry deprotection • CarboxEster → CarboxEster-α-SeR • |
| Reagents: | NaH • SiMe3-CH2X • LiNiPr2 • MoOPH • NaH • MeOTf • Fluoride, cesium • Acrylate • AlHiBu2 • SePh-Cl • AlHiBu2 • Photochemistry • Perbenzoic acid, 3-chloro • |