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Total synthesis of Yomogin:
Reference: Caine, D.; Hasenhuettl, G. Tetrahedron Lett. 1975, 743. DOI
Keywords: Enone → Ketal • O-H → O-SO2R • 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 •

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