Total synthesis of Echninosporin:
| Reference: | Flasz, J. T. ; Hale, K. J. Org. Lett. 2012, 14, 3024-3027. DOI |
| Reactions: | Allyl anion Cycloaddition • Mechanism • Cyclopentene • Bicyclo(430) • Ferrier rearrangement • Ketone → Alkyl-OH • Claisen acylation, carbonate • O-SiEt3 → O-H • CompE+-Si-O/Si-O+H2O • Ketone → Ketone-α-OR • Ketone → Hydrazone • Ketone → Vinyl-X • Hydrazone → I-Vinyl • Barton-McCombie reduction • Pinnick oxidation • Pd-Deallylation • CarboxEster → CarboxAcid (allyl) • Acetal → Aldehyde • Mitsunobu → OC(O)R • Alkyl-OH inversion • Lactone-6 • O-H → O-SiMe2tBu • O-H → O-SiMe2tBu • O-H → O-C(S)OR • O-SiMe2tBu → O-H • CompE+-Si-O/Si-O+H2O • Dehydration → Enoate • CarboxAcid → CarboxEster • O-H → O-SiEt3 • Vinyl-I → Vinyl-H • EneSulfone → Ketone-α-OR • EneSulfone epoxidation, nucleophilic • CarboxAcid → CarboxEster • Williamson esterification • CarboxEster → CarboxAmide • Allyl-OH → Enone • O-C(O)R → O-H • |
| Reagents: | BF3·OEt2 • DMSO, (COCl)2 (Swern) • Sulfinate, benzene • OsO4-22K+ • MgBr2 • OsO4-22K+ • TsOH·Py • S=C(OPh)Cl • HSnBu3 • Hydrazine • I2 • HSnBu3 • TEMPO • Allyl-Br • HSiPhH2 • HBF4 • Allenyl-Sulfone • NaOMe • SiMe2tBu-Cl • NEt3 • SiMe2tBu-OTf • NEtiPr2 • DMAP • NEt3 • AIBN • NEt3 • Pd(PPh3)4 • TsOH·Py • Iodide, R4N+ • Chlorite, sodium • Carbonate, potassium • LiN(SiMe3)2 • Pd(PPh3)4 • DMAP • Carbodiimide • SiEt3-OTf • Lutidine • PBu3, DEAD • 18-crown-6 • Hypochlorite, sodium • Lutidine • HOEt (react)} • |