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Total synthesis of Echninosporin:
Reference: Flasz, J. T. ; Hale, K. J. Org. Lett. 2012, 14, 3024-3027. DOI
Keywords: Allyl-OH → Enone • Allyl anion Cycloaddition • Ferrier rearrangement • Ketone → Alkyl-OH • Claisen acylation, carbonate • O-SiEt3 → O-H • Ketone → Ketone-α-OR • Ketone → Hydrazone • Ketone → Vinyl-X • Barton-McCombie reduction • Pinnick oxidation • CarboxEster → CarboxAcid • CarboxEster → CarboxAmide • Acetal → Aldehyde • Mitsunobu → Ester • O-H → O-SiMe2tBu • O-H → O-SiMe2tBu • O-H → O-C(S)OR • O-SiMe2tBu → O-H • Dehydration → Enoate • CarboxAcid → CarboxEster • O-H → O-SiEt3 • Vinyl-I → Vinyl-H • EneSulfone → Ketone-α-OR • CarboxAcid → CarboxEster • Williamson esterification •
Reagents: BF3·OEt2 • DMSO, (COCl)2 (Swern) • Sulfinate, benzene • BH(sBu3)-Li+ • OsO4-22K+ • OsO4-22K+ • S=C(OPh)Cl • HSnBu3 • I2 • HSnBu3 • TEMPO • Allyl-Br • HSiPhH2 • HBF4 • Allenyl-Sulfone • NaOMe • NEt3 • SiMe2tBu-OTf • NEtiPr2 • DMAP • NEt3 • AIBN • NEt3 • Pd(PPh3)4 • Iodide, R4N+ • Chlorite, sodium • Carbonate, potassium • LiN(SiMe3)2 • Pd(PPh3)4 • DMAP • Carbodiimide • SiEt3-OTf • PBu3, DEAD • 18-cr-6 • Hypochlorite, sodium •

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