image

Total synthesis of Halenaquinone:
Reference: Kienzler, M. A.; Suseno, S.; Trauner, D. J. Am. Chem. Soc. 2008, 130, 8604-8605. DOI
Keywords: Pd-Heck coupling • Cyclohexane • Li/H → Li-Furyl • Alkyl-OH → Ketone • Li-Aryl+Aldehyde • Ketone → Alkyl-OH(asym) • Li-Vinyl+Aldehyde • Allyl-OH → Enone • Quinone synthesis • Diels-Alder, Intram • Naphthoquinone synthesis • Li/Sn → Li-Vinyl • O-H → O-SiPh2tBu • Li-Aryl+CarboxAmide • CarboxAmide+Li-R • Li/I → Li-Aryl • O-SiPh2tBu → O-H •
Reagents: SiPh2tBu-Cl • Imidazole • LiNiPr2 • DMF (react) • Pd(OAc)2 • Fluoride, R4N+ • RuO4-Pr4N+, NMO • High pressure • MnO2 • BuLi(n) • Dess-Martin • BuLi(n) •

Syntheses Home