| Reference: | Kawabata, T.; Grieco, P. A.; Sham, H.-L.; Kim, H.; Jaw, J. Y.; Tu, S. J. Org. Chem. 1987, 52, 3346 DOI |
| Keywords: | O-H -> O-Me Ketone -> Enolsilane Ketone -> Ketone-α-SeR Ketone -> Enolsilane Enolsilane -> Ketone-α-Halo Hydroboration Alkene O-H -> O-SiMe2tBu Alkyl-OH -> Ketone O-SiMe2tBu -> O-H Alkyl-OH -> Aldehyde Aldehyde -> CarboxAcid Ketal -> Ketone Lactone-6 O-H -> O-MOM Ketone -> Enolsilane Saegusa oxidation Enone -> Ketal(thio) O-H -> O-MOM O-MOM -> O-H Allylic oxidation -> Enone Enone enolate+Alkyl-X ConjReduct Enone Selenoxide-Ei -> Enone-6 ConjAdd Cu-R Cu-Vinyl+Enone Ketone -> Ketone-α-Halo Ketone -> Alkene Shapiro reaction Epoxidation, peracid Ketal(thio) -> CH2 Iodolactonization Lactone-6 Alkyl-X -> Alkyl-H Radical reduction(C-I) Lactone -> Lactone-α-OH Ether-5 |
| Reagents: | MeI CrO3·Py2 (Collins) LiNiPr2 MeI Li°/NH3 NH(SiMe3)2 (HMDS) SiMe3-I SePh-Cl H2O2 Vinyl-Li CuI PBu3 NH(SiMe3)2 (HMDS) SiMe3-I NBS DMF (solvent) BH3 H2O2, NaOH DMAP CrO3·Py2 (Collins) Perbenzoic acid, 3-chloro Fluoride, Bu4N+ Hydrazine, tosyl LiNiPr2 CrO3·Py2 (Collins) Ag2O TsOH Cl-CH2-OR NH(SiMe3)2 (HMDS) SiMe3-I Pd(OAc)2 HS-(CH2)2-SH BF3·OEt2 RaNi Hydroxide, sodium NEtiPr2 Cl-CH2-OR Hydroxide, sodium I2 HSnBu3 AIBN LiNiPr2, HMPA MoOPH Me2S BF3·OEt2 |