The first enantioselective synthesis of (-)-conolutinine was achieved in 10 steps. The synthesis featured a catalytic asymmetric bromocyclization of tryptamine to forge the tricycle intermediate. Hydration of an alkene catalyzed by Co(acac) 2 was also employed as a key step to diastereoselectively introduce the tertiary alcohol moiety. The absolute configuration of (-)-conolutinine was established to be (2S,5aS,8aS,13aR) based on this asymmetric total synthesis.
CITATION STYLE
Feng, X., Jiang, G., Xia, Z., Hu, J., Wan, X., Gao, J. M., … Xie, W. (2015). Total Synthesis of (-)-Conolutinine. Organic Letters, 17(18), 4428–4431. https://doi.org/10.1021/acs.orglett.5b02046
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