image

Total synthesis of Twistane:
Reference: Whitlock, H. W., J. Am. Chem. Soc. 1962, 84, 3412. DOI
Keywords: CarboxEster → Alkyl-OH • O-H → O-SO2R • Alkyl-OH → Alkyl-CN • Nitrile → CarboxAcid • Iodolactonization • Lactone-6 • Alkyl-X → Alkyl-H • CarboxEster → Alkyl-OH • O-H → O-SO2R • Wolff-Kishner • Ketone → CH2 • Ketone enolate+Alkyl-X, Intram • Alkyl-X+Enolate •
Reagents: AlH4-Li+ • Sulfonyl chloride, methane • Cyanide, sodium • DMF (solvent) • Glycol • I2 • H2, Pt • NEt3 • AlH4-Li+ • Sulfonyl chloride, methane • DMF (solvent) • NaH • Hydrazine • Hydroxide, potassium •

Syntheses Home