Total synthesis of Croomine:
| Reference: | Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299. DOI |
| Reactions: | Li/H → Li-Furyl • N-Boc → N-H • CarboxEster → CarboxAcid • Li-Aryl+Alkyl-X • Alkyl-X+Li-R • Mannich, vinylogous • Hydrogenation EneLactone • Hydrogenation EneLactone • N-H → N-Alkyl • Amine-7 • Bicyclo(530)-aza • EnolSilane+Iminium • Lactone-5 • Iminium+Enolate • Decarbonylation • Mannich, vinylogous • EnolSilane+Iminium • Iminium+Enolate • Lactone-5 • Mechanism • EnoateEster → Ketene acetal • |
| Reagents: | SiiPr3-OTf • Furyl-Li • BuLi(sec), TMEDA • Acetic acid, trifluoro • H2, Rh • DMF (solvent) • HBr • POCl3 • H2, Pd • HCl, EtOH • SiiPr3-OTf • Morpholine • Furyl-Li • |