Total synthesis of Ikarugamycin (Part 1):
| Reference: | Boeckman, Jr., R. K.; ; Napier, J. J.; Thomas, E. W.; Sato, R. I. J. Org. Chem. 1983, 48, 4152-4154. DOI (Part 2) |
| Reactions: | O-SiMe2tBu → O-H • Alkyl-OH → Alkyl-Br • Decarboxylation β-keto acid • Alkyl-X → Alkyl-I • Finkelstein reaction • Ketone → Ketal • Alkyl-X → Alkyl-PRn • Wittig-alkyl → Ene-cis • Ketal → Diol-1,2 • O-H → O-C(O)R • CarboxEster → Ketene acetal • Claisen-Ireland • CarboxAcid → CarboxEster • CarboxEster → Alkyl-OH • O-H → O-SO2Ar • Alkyl-X → Alkyl-CN • Cyanide+Alkyl-X • Nitrile → Aldehyde • HWE → EnoateEster • Alkyl-OH → Aldehyde • Wittig-alkyl → Ene-cis • Alkene isomerization-EZ • Diels-Alder, Intram, Ene • Cyclohexene • Cyclopentane • Bicyclo(430) • CarboxEster → Alkyl-OH • Ketal → Ketone • O-H → O-SO2Ar • Ketone enolate+Alkyl-X (intram) • Alkyl-X+Enolate (intram) • Bicyclo(330) • O-H → O-SiMe2tBu • CompNu-O-H/O-H+R3Si-X • |
| Reagents: | HBr • Acetic acid • Iodide, sodium • Glycol • TsOH • PPh3 • BuLi(n) • PPh3=CH-Alkyl • BuLi(n) • HCl, H2O • SiMe2tBu-Cl • DMAP • LiNiPr2 • HMPA (solvent) • SiMe3-Cl • Diazomethane • AlHiBu2 • TsCl, Py • Cyanide, potassium • AlHiBu2 • Acetic acid • P(O)(OR)2CH2-C(O)OR' • NaH • Acetic acid • Cr2O7·2PyH (PDC) • I2 • BHT • AlHiBu2 • TsCl, Py • HCl, H2O • KOtBu • PPh3 • BHT • |