Total synthesis of Ircinal A:
| Reference: | Humphrey, J. M.; Liao, Y.; Ali, A.; Rein, T.; Wong, Y.-L.; Chen, H.-J.; Courtney, A. K.; Martin, S. F. J. Am. Chem. Soc. 2002, 124, 8584-92. DOI |
| Reactions: | CarboxAcid → CarboxCl • Allyl-OH → Enal • Enal → Allyl-OH • Pd/Sn-Vinyl+Vinyl-X • Wittig-methyl → Diene • Li-Alkyl+Ketone • Enone+Li-R • Allylic oxidation → Enone • Lactam enolate+CO2 • CarboxEster → Aldehyde • N-C(O)R → N-CH2R • CarboxAcid → CarboxAmide • Pictet-Spengler • Diels-Alder, Intram, Ene • Lactam-6 • Bicyclo(440)-aza • Bicyclo(430)-aza • RCM → Lactam • Lactam-8 • N-H → N-C(O)R • RCM → Ring-N • Amine-9+ • Pyridine synthesis • Allyl-OH → Enal • CarboxAmide → Imine • CompRed-CarboxAmide/Carbamate+M-H • Alkyl-OH → Aldehyde • N-C(O)OR → N-H • Acetal → Enal • O-SiPh2tBu → O-H • Enal → Acetal • EnoateEster → Allyl-OH • O-H → O-C(O)NR2 • Enal → Allyl-OH • |
| Reagents: | LiN(SiMe3)2 • BH4-Na+ • Oxalyl chloride • Pd(PPh3)4 • CrO3 • HCl, MeOH • PPh3=CH2 • AlHiBu2 • Dess-Martin • Orthoformate • Alkyl-Li • AlHiBu2 • Dess-Martin • Acetic acid, trifluoro • DDQ • EneSulfide • CO2 • Hydroxide, potassium • HCl, H2O • Grubbs I • Grubbs I • DMSO, (COCl)2 (Swern) • NEt3 • |