| Reference: | Boeckman, R. K. Jr.; Charette, A. B.; Asberom, T.; Johnston, B. H. J. Am. Chem. Soc. 1987, 109, 7553; DOI |
| Keywords: | O-MOM -> O-H Jones oxidation Alkyl-OH -> CarboxAcid CarboxAcid -> CarboxEster(thio) O-SiMe2tBu -> O-H Jones oxidation Alkyl-OH -> CarboxAcid CarboxEster -> CarboxAcid Simmons-Smith Li/Sn -> Li-Vinyl Li-Vinyl+Alkyl-X Cyclopropane opening Spiroketal Ether-6 CarboxAcid -> CarboxEster(thio) Friedel-Crafts Oxazoline synthesis Li-Sulfide+Borane Li-Sulfide+Borane Li/H -> Li-Vinyl-OR Li-Vinyl -> Sn-Vinyl Metalate rearrangement (B) Dehydration -> Vinyl-OR Ether-6 B-Allyl-Ipc+Aldehyde Sn-Allyl+Aldehyde Ozonolysis Hydroboration Alkene Alkyl-OH -> Alkyl-Br O-H -> O-SiMe2tBu |
| Reagents: | BuLi(n) CH2I2 TsOH CrO3, H2SO4 (Jones) PPh3 Disulfide, pyridyl Pyrrolyl-MgX Fluoride, Bu4N+ CrO3, H2SO4 (Jones) BOP LiSPr Crotyl-SnR3 MgBr2 BH3·THF LiCHR-SPh LiCHR-SPh HgCl2 H2O2 MeSO2Cl, NEt3 SiMe2tBu-Cl O3 Me2S Crotyl-B(Ipc)2 BH3·THF H2O2, NaOH PPh3, CBr4 BuLi, KOtBu SnBu3-Cl Vinyl-SnR3 Imidazole HMPA (solvent) |