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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 • O-H → O-SiMe3 • O-SiMe2tBu → O-H • Ketone+Mg-Alkynyl • Pauson-Khand • Alkene → Diol-1,2 • Diol-1,2 → Carbonate • Pinacol • 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: DMAP • HMPA (solvent) • NH(SiMe3)2 (HMDS) • Alkynyl-MgX • Rh(CO)2Cl • SiMe3-OTf • OsO4 • BF3·OEt2 • Martin sulfurane • HF • Formic acid • O3 • Acetic anhydride • Hydroxide, sodium • SiMe2tBu-OTf • MeI • CO •

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