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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
Keywords: CarboxAmide -> Imine • CarboxAcid -> CarboxCl • EnoateEster -> Allyl-OH • Allyl-OH -> Enal • Enal -> Acetal(Me) • Enal -> Allyl-OH • Allyl-OH -> Enal • Pd/Sn-Vinyl+Vinyl-X • Stille coupling • Wittig-methyl -> Diene • Li-Alkyl+Ketone • Enone+Li-R • Allylic oxidation -> Enone • Lactam enolate+CO2 • CarboxEster -> Aldehyde • CarboxAmide -> Amine • CarboxAcid -> CarboxAmide • Pictet-Spengler • Diels-Alder, Intram • Lactam-6 • Acetal -> Enal • RCM -> Lactam • CarboxAcid -> CarboxAmide • RCM -> Ring-N •
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 • Vinyl-Sulfide • CO2 • Hydroxide, potassium • HCl • Grubbs I • Grubbs I •

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