image

Total synthesis of Solanopyrone:
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
Keywords: O-SiMe2tBu -> O-H • O-H -> O-C(S)NR2 • CompRed-Ketone/CarboxEster+B-H • Ketone -> Alkyl-OH • Xanthate pyrolysis • CarboxEster -> Alkyl-OH • Alkyl-OH -> Aldehyde • Jones oxidation • Ketone-β-OH -> Ketone-1,3-di • Pyrone synthesis • Barton-McCombie reduction • Alkyl-OH -> Alkyl-H • Mukaiyama Aldol • Aldol-Si • Ketene acetal+Aldehyde • Aldehyde+Enolsilane • Ketone epimerization • O-H -> O-C(S)SR • CarboxEster epimerization • Enolsilane -> Ketone enolate • Domino Michael • Vinyl-OH -> Vinyl-OMe • Sulfide -> Sulfoxide • Pummerer •
Reagents: NaOMe • HF • S=C(Im)2 • HSnBu3 • BHsBu3-Li+ • AlH4-Li+ • CrO3Cl·PyH (PCC) • TiCl4 • CrO3, H2SO4 (Jones) • DBU • AIBN • CS2 • MeLi • Crotonate • Formaldehyde • Me2SO4 • Perbenzoic acid, 3-chloro • SiMe3-OTf • Fluoride, Bu4N+

Syntheses Home