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

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