Total synthesis of Haouamine A (Baran):
| Reference: | Burns, N. Z., Krylova, I. N.; Hannoush, R. N.; Baran, P.S. J. Am. Chem. Soc. 2009, 31, 9172-9173 DOI. Prior paper: Baran, P.S.; Burns, N. Z. J. Am. Chem. Soc. 2006, 28, 3908-3909 |
| Reactions: | N-Boc → N-H • Pd/B-Aryl+Vinyl-X • CompE+-Vinyl-I/Alkyl-X+Ar-X(Pd) • Sulfimide-Ei → Enone • Ketone → Enone • Sulfimide-Ei → Enone • Enone enolate+Sulfinyl-Cl • N-H → N-Alkyl • Paracyclophane • Alkyl-X → Alkyl-I • O-Me → O-H (phenol) • |
| Reagents: | B(Br)3 • BuLi(n) • B(OR)3 • Ag2O • Iodide, sodium • Acetic acid, trifluoro • NEtiPr2 • LiN(SiMe3)2 • Imidazole • |