Total synthesis of Stegobinone:
| Reference: | Matteson, D. S.; Man, H.-W.; Ho, O. C. J. Am. Chem. Soc. 1996, 118, 4560 DOI |
| Reactions: | BoronateEster → BoronicAcid • Ketone → EnolBorane • Pyrone synthesis • B-Alkyl → HO-Alkyl • O-Bn → O-H • Alkyl-OH → Ketone • Li-Dichloromethyl+Borane • Li-Dichloromethyl+Borane • Mg-Alkyl+Borane • Borane+Mg-R • Metalate rearrangement (B) • O-Bn → O-H • Metalate rearrangement (B) • Aldol-BR2 → Aldol • Alkyl-OH → Ketone • Alkyl-OH → Ketone-1,3-di • CompOx-Alkyl-OH/B-Alkyl+CrO3 • |
| Reagents: | Chiral auxiliary (boronate) • LiCHCl2 • ZnCl2 • Crotyl-B(Cy2-diol) • Chiral auxiliary (boronate) • NaOBn • LiCHCl2 • Me-MgCl • LiCHCl2 • H2O2 • Hydroxide, sodium • Cr2O7·2PyH (PDC) • Chiral auxiliary (boronate) • B(OTf)BBN • Cr2O7·2PyH (PDC) • H2O2 • Sulfonic acid, methane • RuO4-Pr4N+ • Crotyl-B(Cy2-diol) • Chiral auxiliary (boronate) • Me-MgCl • H2, Pd • Chiral auxiliary (boronate) • B(OTf)BBN • |