image

Total synthesis of Haouamine A:
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
Keywords: Imine -> Amine • N-H -> N-Boc • N-Boc -> N-H • Aryl-OMe -> Aryl-OH • O-C(O)R -> O-H • Ketone enolate+Alkyl-X • Pd/Sn-Vinyl+Aryl-X • Stille coupling • Pyrone synthesis • Alkene Bromoamination • Amine+Alkyl-X • Diels-Alder, Yne • Retro-Diels-Alder, CO2 • Mechanism • Amine-6 • Nitrone -> Hydroxylamine • Amine-5 • Hydrogenolysis N-O • Bredt's Rule • Paracyclophane •
Reagents: KN(SiMe3)2 • Allyl-I • NH2OH • Bromocyclohexadienone • BH4-Na+ • In° • Boc2O • Pd(PPh3)4 • Acetic acid, trifluoro • Carbonate, potassium • BBr3 • Acetic anhydride • Microwave • Carbonate, potassium •

Syntheses Home