Total synthesis of Solanapyrone (MacMillan):
| Reference: | Wilson, R. M.; Jen, W. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 11616. DOI |
| Reactions: | Lactone-6 • Li/H → Li-Pyrone • Diels-Alder, Intram, Ene (asym) • Cyclohexane • Bicyclo(440) • Mukaiyama Aldol • Aldol-Si • Ketene acetal+Aldehyde • Aldehyde+EnolSilane • Li-Vinyl+CarboxEster • Enol → EnolEther • Pyrone synthesis • Alkyl-OH → Ketone-1,3-di • |
| Reagents: | Chiral catalyst (imidazolone) • Imidazole • Butadiene, 1-OR • TiCl4 • Dess-Martin • DBU • MeOTs • Carbonate, potassium • LiNiPr2 • Formate, methyl • DMF (solvent) • |