Total synthesis of Dehydrofukinone:
| Reference: | Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791. DOI |
| Reactions: | EnolSilane → Ketone-α-SeR • Selenoxide-Ei → Enone • Enone → Dienone • Takai-Lombardo → Ene • Ketone → C=CH2 • Brook rearrangement • Silyl ketone Brook • Li-Sulfone+Ketone • Brook rearrangement • Silyl ketone Brook • Diels-Alder, Intram, Ene • Bicyclo(440) • Hydrogenation alkene • Diimide+Alkene • CompRed-Alkene/Enone+Diimide • Mechanism • EnolSilane → Ketone enolate • CompE+-Si-O/Si-O+M-R • Li/I → Li-Vinyl • Li/H → Li-Sulfone • |
| Reagents: | Me-Li • AlEt2-Cl • CH2Br2, Zn°, TiCl4 • SePh-Cl • NHEt2 • Diimide • Hydrazine • Rh(PPh3)3Cl • LiCHR-Sulfonyl • LiNiPr2 • Silyl ketone • Vinyl-Li • BuLi(n) • Silyl ketone • Butadiene, 2-OR • Perbenzoic acid, 3-chloro • LiCHR-Sulfonyl • |