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Total synthesis of Ingenol:
Reference: Jorgensen, L.; McKerral, S. J.; Kuttruff, C. A,; Ungeheuer, F.; Felding, J.; Baran, P. S. Science, 2013, 341, 878 DOI
Keywords: Ketone enolate+Me-I • Rh(CO)2Cl • O-H → O-SiMe3 • O-SiMe2tBu → O-H • Ketone+Mg-Alkynyl • Pauson-Khand • Cycloheptane • Cyclopentenone • Mg-Alkyl+Ketone • Alkene → Diol-1,2 • Diol-1,2 → Carbonate • Pinacol • Cycloheptane • Bicyclo(441) • Allylic oxidation → Allyl-OH • Dehydration → Ene • Allylic oxidation → Allyl-OH • O-H → O-C(O)R • Allylic oxidation → Allyl-Cl • Ozonolysis • Aldehyde+Ketone enolate • O-H → O-SiMe2tBu • Ketone enolate+Me-I •
Reagents: NCS • LiN(SiMe3)2 • Alkynyl-MgX • MeMgBr • SiMe3-OTf • OsO4 • BF3·OEt2 • SeO2 • Martin sulfurane • HF • SeO2 • O3 • Acetic anhydride • Hydroxide, sodium • SiMe2tBu-OTf • MeI • CO • HMPA (solvent) • HMPA (solvent) • Formic acid •

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