Total synthesis of Ipsenol (Yamamoto):
| Reference: | Ikeda, N.; Arai, A.; Yamamoto, H. J. Am. Chem. Soc., 1986, 108, 483. DOI |
| Reactions: | Haloboration Alkyne • Pd/Mg-Vinyl+Vinyl-X • Mg-Allenyl/Propargyl+Borane • Borane+Mg-R • Mg-R → B-R • B-Allenyl-Tartrate+Aldehyde • Aldehyde+B-Allenyl (asym) • B-Vinyl → H-Vinyl • O-THP → O-H • O-H → O-THP • |
| Reagents: | Propargyl-Br • Mg(Hg) • B(OR)3 • Allenyl-BR2 • Tartrate • Acetic acid • H2O2, NaOH • Vinyl-MgX • Pd(PPh3)4 • Allenyl-BR2 • Chiral auxiliary (boronate) • B(Br)BBN • DHP • |