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 |
| Reactions: | Selenide → Selenoxide • Ketone-α-SR → Ketone • Ketal → Ketone • Alkyl-X → Alkyl-I • Finkelstein reaction • Li/H → Li-Dithiane • 2,3-Sigmatropic Selenoxide • Li/Br → Li-Aryl • Li-Dithiane+Epoxide • CompE+-H-Dithiane/H-Furyl+M-R • Cu-Me+Enone • ConjAdd Cu-Me • Li/H → Li-Alkynyl • Li-Allenyl/Propargyl+Alkyl-X • Alkyl-X+Li-R • Li-Alkynyl+Aldehyde • Ketal(thio) → Ketal • Aldehyde → Acetal(thio) • Li-Aryl+CarboxAmide • CarboxAmide+Li-R • O-H → O-SO2Ar • Alkyl-OH → Alkyl-I • Li/H → Li-Allenyl/propargyl • |
| Reagents: | Perbenzoic acid, 3-chloro • Pyridine • Me-Cuprate • Thiol, phenyl • Acetic acid • Epoxide • TsCl, Py • TsNClNa • Glycol • Iodide, sodium • Furyl-Li • BuLi(n) • Thiol, (CH2)3-SH • BuLi(n) • LiNiPr2 • Propargyl-Se • Alkynyl-Li • DMF (react) • |