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Total synthesis of macrocarpines d and e via an enolate-driven copper-mediated cross-coupling process
Replacement of catalytic palladium with copper iodide
Rahman, M. T., Deschamps, J. R., Imer, G. H., Schwabacher, A. W., & Cook, J. M. (2016). Total synthesis of macrocarpines d and e via an enolate-driven copper-mediated cross-coupling process: Replacement of catalytic palladium with copper iodide. Organic Letters, 18(17), 4174-4177. https://doi.org/10.1021/acs.orglett.6b01526
An enolate driven copper-mediated cross-coupling process enabled cheaper and greener access to the key pentacyclic intermediates required for the enantiospecific total synthesis of a number of C-19 methyl substituted sarpagine/macroline indole alkaloids. Replacement of palladium (60-68%) with copper iodide (82-89%) resulted in much higher yields. The formation of an unusual 7-membered cross-coupling product was completely inhibited by using TEMPO as a radical scavenger. Further functionalization led to the first enantiospecific total synthesis of macrocarpines D and E.