Isolation and Total Synthesis of Kirkamide, an Aminocyclitol from an Obligate Leaf Nodule Symbiont.

@article{Sieber2015IsolationAT,
  title={Isolation and Total Synthesis of Kirkamide, an Aminocyclitol from an Obligate Leaf Nodule Symbiont.},
  author={Simon Sieber and Aur{\'e}lien Carlier and Markus Neuburger and Giselher Grabenweger and Leo Eberl and Karl Gademann},
  journal={Angewandte Chemie},
  year={2015},
  volume={54 27},
  pages={
          7968-70
        }
}
The new C7N aminocyclitol kirkamide (1) was isolated from leaf nodules of the plant Psychotria kirkii by using a genome-driven (1)H NMR-guided fractionation approach. The structure and absolute configuration were elucidated by HRMS, NMR, and single-crystal X-ray crystallography. An enantioselective total synthesis was developed, which delivered kirkamide (1) on a gram scale in 11 steps and features a Ferrier carbocyclization and a Pd-mediated hydroxymethylation. We propose that kirkamide is… 

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