Total synthesis of Haouamine A (Baran):
| Reference: | Baran, P.S.; Burns, N. Z. J. Am. Chem. Soc. 2006, 28, 3908-3909 DOI. Following paper: Baran, P.S.; Burns, N. Z. J. Am. Chem. Soc. 2009, 31, 9172-9173 |
| Reactions: | Imine → Amine • Ketone enolate+Alkyl-X • Allyl-X+Enolate • Pd/Sn-Vinyl+Aryl-X • Pyrone synthesis • Alkene Bromoamination • Amine-5 • Bicyclo(330)-aza • N-H → N-Alkyl • Diels-Alder, Yne • Pyrone cycloaddition • Bicyclo(222)-oxa • Retro-Diels-Alder → Arene • Benzene synthesis • Paracyclophane • Mechanism • Amine-6 • Aziridine • Bicyclo(430)-aza • Nitrone → Hydroxylamine • Amine-5 • N-OR → N-H • Bredt's Rule • Paracyclophane • N-Boc → N-H • O-Me → O-H (phenol) • O-H → O-C(O)R (phenol) • O-C(O)R → O-H (phenol) • Ketone → Oxime • N-H → N-Boc • |
| Reagents: | KN(SiMe3)2 • Allyl-I • NH2OH • Bromocyclohexadienone • BH4-Na+ • In° • Boc2O • Pd(PPh3)4 • Acetic acid, trifluoro • Carbonate, potassium • B(Br)3 • Acetic anhydride • Microwave • Carbonate, potassium • |