Total synthesis of Axinellamines New:
| Reference: | Su, S.; Rodriguez, R. A.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 13922-13925. DOI |
| Reactions: | Pauson-Khand • Cyclopentenone • Enone → Allyl-OH • Alkyl-OH → Alkyl-Cl • Allyl-OH → Allyl-Cl • Zn-Allyl+Aldehyde • Alkyl-X → Alkyl-N3 • N-Boc → N-H • N-H → N-C(NR)NR2 • Chloroamination • Alkene → Chloroamine • Spiro(44)-aza • N-C(O)R → N-H • Alkyl-OH → Ketone-α-NR2 • Guanidine synthesis • Enamine → Aminal • Amine → Aminal • Azide → Amine • |
| Reagents: | NMO • Glycol • BH4-Na+, CeCl3 • NCS • PPh3 • Azide, sodium • DMF (solvent) • Acetic acid, trifluoro • Hypochlorite, tbutyl • TfNH2 • Acetic acid, trifluoro • NH2CN • Dioxirane • H2, Pt • Zn° • In° • Dess-Martin • Acetic acid, trifluoro • |