image

Total synthesis of Juvabione:
Reference: Pawson, B. A.; Cheung, H.-C.; Gurbaxani, S.; Saucy, G. J. Am. Chem. Soc. 1970, 92,336-3439. DOI
Keywords: O-H → O-SO2R • Imine → Ketone • O-OH → O-H • CarboxAcid → CarboxEster • Hydroboration Alkene • CompRed-Alkene/Alkene+B-H • Alkyl-X → Alkyl-CN • Li-Alkyl+Nitrile • Nitrile+Li-R → Ketone • Allylic oxidation → Allyl-OH • Allyl-OH → Enal • Aldehyde → CarboxAcid •
Reagents: BH(Siam)2 • H2O2, NaOH • TsCl, Py • Cyanide, sodium • Alkyl-Li • O2 (singlet) • Iodide, sodium • CrO3, H2SO4 (Jones) • Ag2O • Diazomethane • Photochemistry •

Syntheses Home