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| Reference: | Zakarian, A.; Batch, A.; Holton, R. A.. J. Am. Chem. Soc. 2003, 125, 7822-7823. DOI (Part 2) |
| Keywords: | Aldehyde → Alkyl-OH • CarboxEster → CarboxAcid • Henbest • Diol-1,3 → Acetal • EnoateEster → Allyl-OH • Epoxide reduction • CarboxEster → CarboxAcid • Iodolactonization • Lactone-6 • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Alkyl-OH → Alkyl-I • Epoxidation, peracid • CompOx-Alkene/Enoate+Peracid • Lemieux-Johnson oxidation • Alkene cleavage • Lactone-6 • Furst-Plattner diaxial • Sn-Allyl+Allyl-X • Allyl-X+Sn-R • Pd/Zn-Alkyl+Vinyl-X • Alkyne Silyl-metalation • Li-Alkynyl+Alkyl-X • Li/H → Li-Alkynyl • Alkyl-X+Li-R • Epoxidation, halohydrin • CarboxEster → CarboxAcid • O-H → O-SiiPr3 • Hydroboration alkene • Diol-1,3 → Acetal • O-H → O-MOM • Si-Vinyl → I-Vinyl • Vinyl-I → Vinyl-Zn • Acetal → Diol-1,3 • O-Bn → O-H • O-H → O-Tf • O-H → O-SiEt3 • |
| Reagents: | SnBu2(O) • NaH • Camphor sulfonic acid • LiNiPr2 • OsO4, NaIO4 • BH3CN-Na+ • PPh3, I2 • Allyl-SnR3 • BF3·OEt2 • NaOMe • Perbenzoic acid, 3-chloro • Camphor sulfonic acid • AlHiBu2 • AlH4-Li+ • BH3·SMe2 • Camphor sulfonic acid • Chloromethyl ether • Li°/NH3 • Lutidine • CuCN • NIS • Hydroxide, lithium • NIS • SiiPr3-OTf • NaOMe • Allyl-I • Lutidine • Bromoacetate • Allyl-SnR3 • Acrylate • BF3·OEt2 • Zn° • PdCl2(dppf) • Alkynyl-Li • DMPU (solvent) • SiEt3-OTf • |