| Reference: | Ohshima, T.; Xu, Y.; Takita, R.; Shimizu, S. Zhong, D.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 14546-14547. DOI |
| Keywords: | Ketone -> Ketal EnoateEster -> Allyl-OH O-H -> O-SiiPr3 Ketal -> Ketone Ketone epimerization O-H -> O-SEM O-SiiPr3 -> O-H O-H -> O-Tf Imine -> Amine O-PMB -> O-H O-SEM -> O-H Alkyl-OH -> Aldehyde Claisen acylation, Weinreb CarboxEster enolate+CarboxAmide(Weinreb) CarboxAmide(Weinreb)+Enolate Enone enolate+Aldehyde O-H -> O-SiiPr3 Ether-7 O-H -> O-C(O)R N-H -> N-C(O)R O-C(O)R -> O-H Saegusa oxidation Ketone -> Enone Decarboxylation Krapcho Allyl-X+Amine Hydrogenolysis C-S Ketone enamine+Thionium Indole synthesis Mechanism Amine-6 Mukaiyama Aldol Aldol-Si Dehydration -> Enoate Lactam-6 O-H -> O-SiiPr3 Michael(asym) Enone Enone -> Enone-α-Halo Pd/Sn-Aryl+Vinyl-X Stille coupling Ether-7 |
| Reagents: | Chloride, lithium LiNiPr2 Weinreb acetamide BH3CN-Na+ Carbodiimide AlHiBu2 SiiPr3-OTf Camphor sulfonic acid LiTMP Pd2(dba)3 LiNiPr2 Formaldehyde DBU SEM-Cl HF·NEt3 Tf2O Chloride, ammonium Me2S-SMe+ X- BH4-Na+, TiCl4 HCl NiCl2 DMSO, Py·SO3 NaOMe Malonic acid HF·NEt3 Acetic anhydride Yb(OTf)3 NaOMe O=C(OR)2 CuCl BH4-Na+ NEtiPr2 TiCl4 SiMe3-Cl SiMe3-Cl Acetic anhydride SiiPr3-Cl Imidazole DMSO (solvent) Malonate Chiral catalyst KOtBu I2 AsPh3 Aryl-SnR3 DMAP |