Total synthesis of Aquatolide New:
| Reference: | Saya, J. M.; Vos, K.; Kleinnijenhuis, R. A.; van Maarseveen, J. H.; Ingemann, S.; Hiemstra, H. Org. Lett. 2015, 17, 3892-3894. DOI |
| Reactions: | Crabbe homologation • Alkyne → Allene • Li-Phosphonate+Alkyl-X • CarboxEster enolate+Alkyl-X • CarboxEster → CarboxAcid • Aldol-Ti • Aldehyde → Acetal(Me) • Aldehyde → Acetal(Me) • CompE+-Aldehyde/Ketone+glycol • O-H → O-C(O)R • HWE → EnoateEster (intram) • Lactone-6 • Photochemistry 2+2 • Cyclobutane • Bicyclo(211) • Lactone-5 • Bicyclo(211) • Hydroboration → Alkyl-OH • CompRed-Alkene/CarboxEster+M-H • Alkyl-OH → Aldehyde • Mg-Alkyl+Aldehyde • Aldehyde+Mg-R • CompE+-Aldehyde/CarboxEster+M-R • O-Bn → O-H • Alkyl-OH → Aldehyde • Alkyl-OH → Ketone • Mukaiyama Aldol • Aldol-Si • Aldehyde+EnolSilane • Cyclooctane • Bicyclo(511) • Ketone → EnolSilane • Dehydroalkoxylation → Enone • |
| Reagents: | NaH • Hydroxide, potassium • Ti(OiPr)4 • KOtBu • Propiolaldehyde • Orthoformate • TsOH • Carbodiimide • DMAP • NaH • HCl, H2O • Formaldehyde • NHCy2 • CuI • Photochemistry • Acetone (solvent) • BH3·THF • H2O2, NaOH • Dess-Martin • Alkyl-MgBr • H2, Pd • Dess-Martin • Orthoformate • CeCl3 • LiN(SiMe3)2 • SiMe3-Cl • BF3·OEt2 • TsOH • |