AI Article Synopsis
- The study explores the addition of a critical exocyclic enone to the natural alkaloid (-)-eburnamonine, enhancing its chemical properties and biological function.
- The modification significantly increases its anticancer activity and reactivity with nucleophilic thiols, assessed using quantitative NMR without deuterated solvents.
- The synthetic method achieved a 40% overall conversion rate, employing a modified Peterson olefination technique to effectively introduce the enone despite substantial steric hindrance.
Article Abstract
The biological role of installing a critical exocyclic enone into the structure of the alkaloid, (-)-eburnamonine, and characterization of the new chemical reactivity by quantitative NMR without using deuterated solvents are described. This selective modification to a natural product imparts potent anticancer activity as well as bestows chemical reactivity toward nucleophilic thiols, which was measured by quantitative NMR. The synthetic strategy provides an overall conversion of 40%. In the key synthetic step, a modified Peterson olefination was accomplished through the facile release of trifluoroacetate to create the requisite enone in the presence of substantial steric hindrance.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3867447 | PMC |
| http://dx.doi.org/10.1016/j.bmcl.2013.08.095 | DOI Listing |
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