Total synthesis of Yomogin:
| Reference: | Caine, D.; Hasenhuettl, G. Tetrahedron Lett. 1975, 743. DOI |
| Reactions: | Enone → Ketal • O-H → O-SO2Me • Ketone → EnAmine • CompE+-Ketone/Enone+Amine • Ketone enamine+Alkyl-X • Bromoacetate+EnAmine • Alkyl-X+EnAmine • Lactone enolate+Aldehyde • Dehydration → EneLactone • Ketone → Enone • Ketone → Alkyl-OH • CompRed-Ketone/Enone+M-H • Lactone-5 • Ketal → Enone • |
| Reagents: | Pyrrolidine • Bromoacetate • Acetic acid • BH(sBu3)-K+ • Glycol • TsOH • LiNiPr2 • Formaldehyde • Sulfonyl chloride, methane, Py • Pyridine • TsOH • Acetone (solvent) • DDQ • |