Total synthesis of Azamerone:
| Reference: | Landry, M. L.; McKenna, G. M.; Burns, N. Z. J. Am. Chem. Soc. 2019, 141, 2867-2871. DOI |
| Reactions: | Resolution • O-SiMe2tBu → O-H (phenol) • CompE+-Si-O/Si-O+H2O • O-C(O)R → O-H • Cationic cyclization • Cyclohexane • O-H → O-Tf • Dehydrosulfonoxylation → Ene • CompE+-Alkyl-X/Alkyl-X+Base • Hydroboration → Alkyl-B • Chloroetherification • Ether-6 • Bicyclo(440)-oxa • Enol → Vinyl-Cl • Ketone → Hydrazone • Hydrazone → Diazo • Pd/B-Alkyl+Aryl-X • Diels-Alder, Enone • Tetrazine Cycloaddition • Retro-Diels-Alder → Diene • Pyridazine synthesis • O-SiMe2tBu → O-H • Aryl-Cl → Aryl-H • O-H → O-SiMe2tBu • Phenol → Quinol • Quinone synthesis • |
| Reagents: | Cl2 • Chloride, lithium • Tf2O • DBU • BH3·SMe2 • Ti(OiPr)3Cl • Hypochlorite, tbutyl • Chiral catalyst (diol) • HClO4 • Oxalyl chloride • DMF (solvent) • Hydrazine, tosyl • Hydroxide, sodium • Carbonate, potassium • SiMe2tBu-OTf • Hydroxide, sodium • Iodosobenzene-TFA • O2 • HCl • Carbonate, potassium • NEtiPr2 • Lutidine • |