Total synthesis of Ikarugamycin (Part 2):
| Reference: | Boeckman, Jr., R. K.; Weidner, C. H.; Perni, R. B.; Napier, J. J. J. Am. Chem. Soc. 1989, 111, 8036–8037. DOI (Part 1) |
| Reactions: | Ketone → Ketone-α-OR • Ketone-α-OH cleavage • Criegee oxidation • Aldehyde → Acetal(Me) • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Aldehyde epimerization • HWE → Diene • Acetal → Aldehyde • CompNu-Acetal/Ketal+H+ • HWE → EnoateEster • Pd-Deallylation • CarboxEster → CarboxAcid (allyl) • Pd-Deallylation • N-C(O)OR → N-H • Claisen acylation, ester • CarboxEster enolate+CarboxEster • N-H → N-C(O)R • Lactam-9+ • N-Bn → N-H • |
| Reagents: | Iodosobenzene-OAc • Hydroxide, potassium • Pb(OAc)4 • Amberlyst • HOMe (react) • AlHiBu2 • Cr2O7·2PyH (PDC) • DBU • P(O)(OR)2CH2-Vinyl • KN(SiMe3)2 • Amberlyst • P(O)(OCH2CF3)2CH2-C(O)OMe • Carbonate, potassium • 18-crown-6 • Acetate, ammonium • DMAP • Pd(PPh3)4 • KOtBu • Acetic acid, trifluoro • |