image

Total synthesis of Dolabellatrienone:
Reference: Corey, E. J.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 1229. DOI
Keywords: Epoxide -> Diol • Diol-1,2 cleavage • Aldehyde -> Alkyl-OH • Alkyl-OH -> Alkyl-I • O-SiPh2tBu -> O-H • CarboxAcid -> Alkyl-OH • Alkyl-OH -> Aldehyde • Alkyl-OH -> Aldehyde • Pinnick oxidation • Aldehyde -> CarboxAcid • CarboxAcid -> CarboxCl • Li/Br -> Li-Vinyl • Yamaguchi lactonization • Lactone-15+ • Wittig-isopropyl • Friedel-Crafts Acylation, Ene • Li-Vinyl+Alkyl-X • Hydrohafnation, Ene -> Alkyl-OH • Nitrile -> CarboxAcid • Alkyl-X -> Alkyl-CN • Claisen(asym) •
Reagents: BuLi(tert) • Vinyl-Li • HMPA (solvent) • Periodate, sodium • BH4-Na+ • PPh3, I2 • Cyanide, sodium • Fluoride, Bu4N+ • Hydroxide, potassium • Benzoyl chloride, 2,4,6-trichloro • NEt3 • Corey diazaborolidine • AlH4-Li+ • Dess-Martin • PPh3=CMe2 • HfCp2HCl • Hydroperoxide, tbutyl • Dess-Martin • Chlorite, sodium • Oxalyl chloride • DBU • NEt3 • DMAP • DMAP • DMF (solvent) •

Syntheses Home