| Reference: | Stork, G.; Niu, D.; Fujimoto. A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R.; Dake, G. R. J. Am. Chem. Soc. 2001, 123, 3239. DOI |
| Keywords: | O-H -> O-SiMe2tBu O-SiMe2tBu -> O-H Lactone-5 Lactone -> Lactol Imine -> Amine O-SiPh2tBu -> O-H O-H -> O-SO2R Benzyl-H -> Benzyl-OH Allylic oxidation -> Allyl-OH Li-Benzyl+O2 Wittig-methoxymethyl Reductive formylation Mitsunobu -> Azide Alkyl-OH -> Alkyl-N3 CarboxAmide enolate+Alkyl-X Li-Benzyl+Aldehyde Aldehyde+Li-R CompE+-Aldehyde/Azide+Li-R Amine+Alkyl-X Amine-6 Alkyl-OH -> Ketone Staudinger Azide -> Amine Ketone -> Imine Amine-6 |
| Reagents: | AlMe3 SiMe2tBu-Cl LiNiPr2 Iodoethanol TsOH·Py AlHiBu2 PPh3=CH-OMe PPh3, DEAD HCl, H2O Benzyl-Li BH4-Na+ HF MeSO2Cl NaH Azide, diphenylphosphoryl AlMe2-NR2 Imidazole DMSO (solvent) DMSO, (COCl)2 PPh3 |