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Total synthesis of Myoporone, 7-Hydroxy:
Reference: Reich, H. J.; Shah, S. K.; Gold, P. M.; Olson, R. E. J. Am. Chem. Soc., 1981, 103, 3112. DOI
Keywords: Ketal → Ketone • O-H → O-SO2R • Ketal(thio) → Ketal • Alkyl-OH → Alkyl-I • Finkelstein reaction • Li-Aryl+CarboxAmide • CarboxAmide+Li-R • Aldehyde → Acetal(thio) • Li/H → Li-Dithiane • 2,3-Sigmatropic Selenoxide • Li/Br → Li-Aryl • Li-Dithiane+Epoxide • Cu-Me+Enone • ConjAdd Cu-R • Li/H → Li-Alkynyl • CompE+-H-Dithiane/H-Furyl+Li-R • Li-Allenyl/Propargyl+Alkyl-X • Alkyl-X+Li-R • Li-Alkynyl+Aldehyde •
Reagents: Perbenzoic acid, 3-chloro • Pyridine • LiCuMe2 • Thiol, phenyl • Acetic acid • Epoxide • TsCl, Py • TsNClNa • Glycol • Iodide, sodium • BuLi(n) • DMF (react) • Thiol, (CH2)3-SH • BuLi(n) • LiNiPr2 • Propargyl-Se • Furyl-Li • Alkynyl-Li •

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