Total synthesis of Himbacene:
| Reference: | Tchabanenko, K.; Adlington, R. M.; Cowley, A. R.; Baldwin, J. E. Org. Lett. 2005, 7, 585. DOI |
| Reactions: | Imine → Ketone • Amine-6 • Peterson → Enal • HWE → Enone • Reductive amination, B-H • Eschweiler-Clarke methylation • Diels-Alder, Intram, Ene • Bicyclo(440) • Li-Phosphonate+CarboxAmide • Aldehyde azaenolate+Aldehyde • Reductive amination, B-H • Amine-6 • N-H → N-Boc • N-Boc → N-H • Amine → CarboxAmide • |
| Reagents: | ZnBr2 • Boc2O • RuO4 • Periodate, sodium • NEtiPr2 • Acetic acid, trifluoro • BH3CN-Na+ • BH3CN-Na+ • Formaldehyde • ZnCl2 • P(O)(OR)2CH2-C(O)R' • |