Total synthesis of Bigelovin:
| Reference: | Grieco, P. A.; Ohfune, Y.; Majetich, G. J. Org. Chem. 1979, 44, 3092. DOI |
| Reactions: | O-THP → O-H • Aldol-Li → Aldol • Lactone enolate+Aldehyde • Aldehyde+Lactone enolate • Epoxidation, peracid • CompOx-Alkene/Alkene+Peracid • CarboxAcid enolate+Epoxide • Epoxide+Enolate • Allyl-OH → Enone • CompOx-Allyl-OH/Alkyl-OH+MnO2 • Enone → Allyl-OH • O-Bn → O-H • Lactone-5 • O-H → O-THP • Henbest • Dehydrosulfonoxylation → EnoateEster • O-H → O-C(O)R • |
| Reagents: | AlH4-Li+ • Li°/NH3 • HCl, H2O • Formaldehyde • Sulfonyl chloride, methane • Acetic acid • MnO2 • Acetic anhydride, DMAP • LiNiPr2 • CH2=C(OLi)2 • Perbenzoic acid, 3-chloro • DHP • |