Total synthesis of Juvabione (Pawson):
| Reference: | Pawson, B. A.; Cheung, H.-C.; Gurbaxani, S.; Saucy, G. J. Am. Chem. Soc. 1970, 92,336-3439. DOI |
| Reactions: | O-H → O-SO2Ar • O-OH → O-H • Hydroboration → Alkyl-OH • CompRed-Alkene/Alkene+M-H • Alkyl-X → Alkyl-CN • Li-Alkyl+Nitrile • Nitrile+Li-R → Ketone • Allylic oxidation → Allyl-OH • Singlet oxygen+Alkene • Allyl-OH → Enal • Aldehyde → CarboxAcid • CarboxAcid → CarboxEster • Imine → Ketone • |
| Reagents: | BH(Siam)2 • H2O2, NaOH • TsCl, Py • Cyanide, sodium • Alkyl-Li • O2 (singlet) • Iodide, sodium • CrO3, H2SO4 (Jones) • Ag2O • Diazomethane • Photochemistry • |