image

Total synthesis of Spongian-16-one:
Reference: Pattenden, G.; Roberts, L. Tetrahedron Lett. 1996, 37, 4191. DOI
Keywords: O-H -> O-THP • O-THP -> O-H • Alkyl-OH -> Aldehyde • Pinnick oxidation • Aldehyde -> CarboxAcid • Sulfoxide-Ei -> EneLactone • Lactone -> EneLactone • Li/Br -> Li-Alkyl • Li-Alkyl+Ketone • Simmons-Smith • Hydrogenolysis Cyclopropane • Nozaki-Takai -> Ene • Ketone -> C=CH2 • Lactone enolate+Alkyl-X • Lactone-5 • Cyclopropylcarbinyl cation • Alkyl-X -> Alkyl-I • Finkelstein reaction • Radical cyclization(Acyl) •
Reagents: HSnBu3 • AIBN • Alkyl-Li • Li°/THF • HBr • DHP • Iodide, sodium • Perbenzoic acid, 3-chloro • Carbonate, calcium • Dess-Martin • Chlorite, sodium • SePh-Phthalimide • CH2Br2, Zn°, TiCl4 • CH2I2, Zn/Cu • H2, Pt • Acetic acid •

Syntheses Home