Total synthesis of Serricornin:
| Reference: | Matteson, D. S.; Singh, R. P. J. Org. Chem. 1998, 63, 4466. DOI |
| Reactions: | Alkene cleavage • Li-Dichloromethyl+Borane • Mg-Alkyl+Borane • Borane+Mg-R • Metalate rearrangement (B) • Lemieux-Johnson oxidation • B-Vinyl → H-Vinyl • Alkyne Haloboration • Li-Dichloromethyl+Borane • Li-Chloromethyl+Borane • Mg-Vinyl+Borane • Borane+Mg-R • Metalate rearrangement (B) • Alkyne → Vinyl-Br • B-Alkyl → HO-Alkyl • |
| Reagents: | Crotyl-B(Cy2-diol) • Chiral auxiliary (boronate) • LiCHCl2 • Me-MgCl • LiCHCl2 • Alkyl-MgX • H2O2, NaOH • B(Br)3 • Vinyl-BR2 • Acetic acid • Vinyl-Br • Mg° • OsO4, NaIO4 • Chiral auxiliary (boronate) • LiCHCl2 • ZnCl2 • Crotyl-B(Cy2-diol) • LiCH2-Cl • Vinyl-MgX • Crotyl-B(Cy2-diol) • Chiral auxiliary (boronate) • Chiral auxiliary (boronate) • Vinyl-MgX • |