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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 • Alkyl-X+Enolate • 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 •

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