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Total synthesis of Crotogoudin:
Reference: Breitler, S.; Carreira, E. M. Angew. Chem. Int. Ed. 2013, 52, 11168–11171. DOI
Keywords: O-Bn → O-H • Propenyl-MgX • Iodonium • O-SiMe2tBu → O-H • Michael Enal • Robinson annulation, ketoester • Aldol-Base → Enone • Cyclohexenone • Decarboxylation Krapcho • ConjReduct Enone • Aldol-H+ → Aldol • Bicylo(222) • Cyclohexanone • Cyclopropane • Radical cyclization(Ketyl) • Reductive elimination - X/OR • Lactone-6 • Decarboxylation Krapcho • Mannich • Iminium+Enolate • Mg-Vinyl+Ketone • Ketone+Mg-Vinyl • Hofmann elim → Enone • Ketone → Alkyl-OH(asym) • Allylic oxidation → Allyl-OH • O-H → O-C(O)R • O-H → O-SiMe2tBu • CompNu-Alcohol/Alcohol+R3Si-X • Lactone-5 • Alkyl-OH → Ketone • Lactone → Ketene acetal • Alkyl-OH → Aldehyde • Alkyl-OH → Ketone •
Reagents: DBU • Chloride, lithium • Na°/NH3 • Oxalyl chloride • NEt3 • HCl • Dess-Martin • Baker's yeast • Chloride, lithium • SiMe2tBu-OTf • Iodonium ylide • Bicarbonate, sodium • SeO2 • Hydroperoxide, tbutyl • BH4-Na+ • DMAP • SmI2 • DMPU (solvent) • Chloride, lithium • HCl • Dess-Martin • SiiPr3-OTf • NEt3 • LiN(SiMe3)2 • MeI • Al2O3 • CH2=NMe2+I-

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