Total synthesis of Imperanene:
| Reference: | Shattuk, J. C.; Shreve, C. M.; Solomon, S. E. Org. Lett. 2001, 3, 3021. DOI |
| Reactions: | Ozonolysis C=N • Wittig-benzyl → Styrene • Hydroboration → Alkyl-OH • SAMP hydrazone • Aldehyde → Hydrazone • Aldehyde azaenolate+Alkyl-X (asym) • Alkyl-X+Azaenolate • O-H → O-SiMe2tBu (phenol) • Alkyl-OH → Aldehyde • O-Bn → O-H • O-SiMe2tBu → O-H (phenol) • |
| Reagents: | SiMe2tBu-Cl • BH(Siam)2 • CrO3Cl·PyH (PCC) • O3 • PPh3=CH-Ar • SPh-SiMe3 • Fluoride, R4N+ • Imidazole • LiNiPr2 • Chloromethyl ether • Chiral auxiliary (hydrazone-SAMP) • |