Total synthesis of Solanapyrone (Hagiwara):
| Reference: | Hagiwara, H.; Kobayashi, K.; Miya, S.; Hoshi, T.; Suzuki, T.; Ando, M.; Okamoto, T.; Kobayashi, M.; Yamamoto, I.; Ohtsubo, S.; Kato, M.; Uda, H.J. Org. Chem. 2002, 67, 5969. DOI |
| Reactions: | Xanthate pyrolysis • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Barton-McCombie reduction • Alkyl-OH → Alkyl-H • Mukaiyama Aldol • Aldol-Si • Ketene acetal+Aldehyde • Aldehyde+EnolSilane • Ketone epimerization • CarboxEster epimerization • EnolSilane → Ketone enolate • ConjAdd-Michael • Cyclohexanone • Bicyclo(440) • Diels-Alder, EnoateEster • Enol → EnolEther • Sulfide → Sulfoxide • Pummerer • Pyrone synthesis • O-SiMe2tBu → O-H • O-H → O-C(S)NR2 • O-H → O-C(S)SR • Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • Alkyl-OH → Ketone-1,3-di • Jones oxidation • |
| Reagents: | NaOMe • HF • S=C(Imid)2 • HSnBu3 • BH(sBu3)-Li+ • KOtBu • AlH4-Li+ • CrO3Cl·PyH (PCC) • Butadiene, 1-OR • Butadiene, 2-OR • TiCl4 • CrO3, H2SO4 (Jones) • DBU • AIBN • CS2 • Butadiene, 2-OR • Me-Li • Crotonate • Formaldehyde • Sulfate, dimethyl • Perbenzoic acid, 3-chloro • SiMe3-OTf • Fluoride, R4N+ • |