Total synthesis of Sterpurine:
| Reference: | Harmata, M.; Bohnert, G. J. Org. Lett. 2003, 5, 59. DOI |
| Reactions: | Regitz diazo transfer • Photochemistry • Mg-Silane • Peterson, Vinylogous • Favorskii • Cyclobutane • Bicyclo(420) • Bicyclo(430) • Diazoketone → Ketene • Cyclopentanone • Cu-Alkyl+EnoateEster • EnoateEster+Cu-R • ConjAdd-Elimination • ConjAdd Cu-Alkyl • Mg-R → Cu-R • Allylic oxidation → Enone • Li-Me+Ketone • Ketone+Li-Alkyl • Dehydration → Ene • Hydroboration → Alkyl-OH • Diazoketone • Ketone → EnolTriflate • Enone → Alkene • Diazene rearrangement • Hydrazone reduction • Alkyl-OH → Alkyl-I • Alkyl-X → Alkyl-H • Aldehyde → CH3 • Li/I → Li-Alkyl • Oxyallyl Cycloaddition • Bicyclo(421) • Cyclopentanone • Ketone → Alkyl-OH • Ketone → Hydrazone • EnoateEster → Allyl-OH • Alkyl-OH → Ketone • Aldehyde → Alkyl-OH • Ketene+Alcohol • |
| Reagents: | Azide, sulfonyl • NEt3 • Diazoketone • Photochemistry • HOMe (react) • Tf2O • MgCH2-SiMe3 • CuBr • AlH4-Li+ • SiO2 • AlH4-Li+ • KH • Carbodiimide • BuLi(tert) • CrO3, DMP • Hydrazine, tosyl • BH(Catechol) • BH3·THF • CrO3Cl·PyH (PCC) • Me-Li • SOCl2 • AlH4-Li+ • CF3CH2OH (solvent) • NEt3 • |