Abstract:
:Many natural products that contain basic nitrogen atoms--for example alkaloids like morphine and quinine-have the potential to treat a broad range of human diseases. However, the presence of a nitrogen atom in a target molecule can complicate its chemical synthesis because of the basicity of nitrogen atoms and their susceptibility to oxidation. Obtaining such compounds by chemical synthesis can be further complicated by the presence of multiple nitrogen atoms, but it can be done by the selective introduction and removal of functional groups that mitigate basicity. Here we use such a strategy to complete the chemical syntheses of citrinalin B and cyclopiamine B. The chemical connections that have been realized as a result of these syntheses, in addition to the isolation of both 17-hydroxycitrinalin B and citrinalin C (which contains a bicyclo[2.2.2]diazaoctane structural unit) through carbon-13 feeding studies, support the existence of a common bicyclo[2.2.2]diazaoctane-containing biogenetic precursor to these compounds, as has been proposed previously.
journal_name
Naturejournal_title
Natureauthors
Mercado-Marin EV,Garcia-Reynaga P,Romminger S,Pimenta EF,Romney DK,Lodewyk MW,Williams DE,Andersen RJ,Miller SJ,Tantillo DJ,Berlinck RGS,Sarpong Rdoi
10.1038/nature13273subject
Has Abstractpub_date
2014-05-15 00:00:00pages
318-324issue
7500eissn
0028-0836issn
1476-4687journal_volume
509pub_type
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