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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-9+ • Wittig-isopropyl • Friedel-Crafts Acylation, Ene • Li-Vinyl+Alkyl-X • Alkyl-X+Li-R • 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, R4N+ • 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) •

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