Total synthesis of Conduritol B, F:
| Reference: | Heo, J. N.; Holson, E. B.; Roush, W. R. Org. Lett. 2003, 5, 1697-1700. DOI |
| Reactions: | O-Bn → O-H • O-Bn → O-H • O-Bn → O-H • RCM → Ring-C • Cyclohexene • Si-Alkyl → HO-Alkyl • Peterson → Ene • B-Allyl-Ipc+Aldehyde • Aldehyde+B-Allyl (asym) • Alkene → Diol-1,2 • Peterson → Ene • |
| Reagents: | OsO4, NMO • KN(SiMe3)2 • 18-crown-6 • H2SO4 • Hg(OAc)2 • Peracetic acid • Na°/NH3 • Na°/NH3 • Na°/NH3 • Grubbs II • Vinyl-SiR3 • Allyl-B(Ipc)2 • Chiral auxiliary (boronate) • |