Total synthesis of Twistane:
| Reference: | Whitlock, H. W., J. Am. Chem. Soc. 1962, 84, 3412. DOI |
| Reactions: | Wolff-Kishner • Ketone → CH2 • Ketone enolate+Alkyl-X (intram) • Alkyl-X+Enolate (intram) • Cyclohexanone • O-H → O-SO2Me • CompNu-O-H/O-H+RSO2X • CarboxEster → Alkyl-OH • Bicyclo(222) • Alkyl-X → Alkyl-CN • Nitrile → CarboxAcid • Iodolactonization • Lactone-6 • Alkyl-X → Alkyl-H • CarboxEster → Alkyl-OH • O-H → O-SO2Me • |
| Reagents: | AlH4-Li+ • Sulfonyl chloride, methane, Py • Cyanide, sodium • DMF (solvent) • Glycol • I2 • H2, Pt • NEt3 • AlH4-Li+ • Sulfonyl chloride, methane, Py • DMF (solvent) • NaH • Hydrazine • Hydroxide, potassium • |