Total synthesis of Sparteine (Aube):
| Reference: | Smith, B. T.; Wendt, J. A.; Aube, J. Org. Lett. 2002, 4, 2577. DOI |
| Reactions: | N-Boc → N-H • Photochemistry electrocyclic • Aldol-Li → Enone • Ketone enolate+Aldehyde • Ketone enolate+Alkyl-X (intram) • Alkyl-X+Enolate (intram) • Hydrogenation alkene • Enone → Ketone • Mitsunobu → Azide • Alkyl-OH → Alkyl-N3 • Nitrone → Oxaziridine • Amine-6 • N-C(O)R → N-CH2R • Amine-6 • Bicyclo(331)-aza • N-C(O)R → N-CH2R • CompE+-CarboxAmide/Ketone+Lawesson • Si-Alkyl → HO-Alkyl • N-H → N-Alkyl • Alkyl-X → Alkyl-I • Finkelstein reaction • Lactam-7 • Amine-6 • Schmidt reaction • Lactam-7 • Amine-6 • Bicyclo(321)-aza • Ketone → Nitrone • Ketone → Ketal • CarboxAmide → Thioamide • Alkyl-OH → Ketone • Pd-Hydrosilylation • |
| Reagents: | H2O2 • DMSO, (COCl)2 (Swern) • Glycol • LiNiPr2 • Sulfonyl chloride, methane • H2, Pd • Azide, zinc • PPh3, DEAD • Lawesson • RaNi • LiNiPr2 • Iodide, sodium • NHBoc2 • Carbonate, potassium • Acetic acid • Bicarbonate, sodium • Photochemistry • AlH4-Li+ • PdCl(Allyl) • DBU • DMF (solvent) • TiCl4 • |