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Total synthesis of Sterpurine:
Reference: Harmata, M.; Bohnert, G. J. Org. Lett. 2003, 5, 59. DOI
Keywords: Regitz diazo transfer • Photochemistry • EnoateEster → Allyl-OH • Peterson, Vinylogous • Ketone → Alkyl-OH • Alkyl-OH → Ketone • Li-Me+Ketone • Ketone+Li-Alkyl • Favorskii • Cyclobutane • Wolff rearrangement • Cu-Alkyl+EnoateEster • EnoateEster+Cu-R • ConjAdd-Elimination • ConjAdd Cu-R • Allylic oxidation → Enone • Li-Me+Ketone • Ketone+Li-Alkyl • Dehydration → Ene • Hydroboration alkene • Diazoketone • Ketone → EnolTriflate • Enone → Alkene • Alkyl-OH → Alkyl-I • Alkyl-X → Alkyl-H • Aldehyde → Alkyl-OH • Oxyallyl Cycloaddition •
Reagents: Azide, sulfonyl • NEt3 • Diazoketone • Photochemistry • Tf2O • MgCH2-SiMe3 • CuBr • AlH4-Li+ • HCl • AlH4-Li+ • KH • Carbodiimide • BuLi(tert) • CrO3, DMP • Hydrazine, tosyl • BH(Catechol) • BH3·THF • CrO3Cl·PyH (PCC) • MeLi • SOCl2 • AlH4-Li+ • CF3CH2OH(solvent) • NEt3

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