Total synthesis of Grandisol:
| Reference: | Stork, G.; Cohen, J. F. J. Am. Chem. Soc 1974, 96, 5270. DOI |
| Reactions: | Nitrile anion+Alkyl-X • Wolff-Kishner • Aldehyde → CH3 • Wittig-methyl • Nitrile anion+Epoxide • Epoxide+Nitrile anion (intram) • Epoxidation, peracid • CompOx-Alkene/Nitrile+Peracid • Cyclobutane • Nitrile → Aldehyde • Jones oxidation • Alkyl-OH → Ketone • O-THP → O-H • |
| Reagents: | LiNiPr2, HMPA • Bromoethanol • AlHiBu2 • Hydrazine • Hydroxide, potassium • CrO3, H2SO4 (Jones) • PPh3=CH2 • BuLi(n) • HCl, THF • LiN(SiMe3)2 • Perbenzoic acid, 3-chloro • |