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Total synthesis of Solanapyrone:
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 • Alkyl-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 • ConjAdd-Michael • Enol → EnolEther • Sulfide → Sulfoxide • Pummerer •
Reagents: NaOMe • HF • S=C(Imid)2 • HSnBu3 • BH(sBu3)-Li+ • AlH4-Li+ • CrO3Cl·PyH (PCC) • TiCl4 • CrO3, H2SO4 (Jones) • DBU • AIBN • CS2 • MeLi • Crotonate • Formaldehyde • Sulfate, dimethyl • Perbenzoic acid, 3-chloro • SiMe3-OTf • Fluoride, R4N+

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