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A concise synthesis of (+)-batzelladine B from simple pyrrole-based starting materials

Overview of attention for article published in Nature, September 2015
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About this Attention Score

  • In the top 5% of all research outputs scored by Altmetric
  • High Attention Score compared to outputs of the same age (97th percentile)
  • Above-average Attention Score compared to outputs of the same age and source (54th percentile)

Mentioned by

news
8 news outlets
blogs
1 blog
twitter
12 X users
facebook
1 Facebook page

Citations

dimensions_citation
55 Dimensions

Readers on

mendeley
88 Mendeley
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Title
A concise synthesis of (+)-batzelladine B from simple pyrrole-based starting materials
Published in
Nature, September 2015
DOI 10.1038/nature14902
Pubmed ID
Authors

Brendan T. Parr, Christos Economou, Seth B. Herzon

Abstract

Alkaloids, secondary metabolites that contain basic nitrogen atoms, are some of the most well-known biologically active natural products in chemistry and medicine. Although efficient laboratory synthesis of alkaloids would enable the study and optimization of their biological properties, their preparation is often complicated by the basicity and nucleophilicity of nitrogen, its susceptibility to oxidation, and its ability to alter reaction outcomes in unexpected ways-for example, through stereochemical instability and neighbouring group participation. Efforts to address these issues have led to the invention of a large number of protecting groups that temper the reactivity of nitrogen; however, the use of protecting groups typically introduces additional steps and obstacles into the synthetic route. Alternatively, the use of aromatic nitrogen heterocycles as synthetic precursors can attenuate the reactivity of nitrogen and streamline synthetic strategies. Here we use such an approach to achieve a synthesis of the complex anti-HIV alkaloid (+)-batzelladine B in nine steps (longest linear sequence) from simple pyrrole-based starting materials. The route uses several key transformations that would be challenging or impossible to implement using saturated nitrogen heterocycles and highlights some of the advantages of beginning with aromatic reagents.

X Demographics

X Demographics

The data shown below were collected from the profiles of 12 X users who shared this research output. Click here to find out more about how the information was compiled.
Mendeley readers

Mendeley readers

The data shown below were compiled from readership statistics for 88 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Japan 2 2%
Italy 1 1%
Unknown 85 97%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 27 31%
Researcher 16 18%
Student > Bachelor 9 10%
Student > Doctoral Student 7 8%
Professor 6 7%
Other 16 18%
Unknown 7 8%
Readers by discipline Count As %
Chemistry 71 81%
Unspecified 1 1%
Agricultural and Biological Sciences 1 1%
Biochemistry, Genetics and Molecular Biology 1 1%
Psychology 1 1%
Other 1 1%
Unknown 12 14%
Attention Score in Context

Attention Score in Context

This research output has an Altmetric Attention Score of 73. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 07 July 2016.
All research outputs
#504,366
of 23,577,761 outputs
Outputs from Nature
#22,471
of 92,664 outputs
Outputs of similar age
#6,770
of 246,287 outputs
Outputs of similar age from Nature
#461
of 1,006 outputs
Altmetric has tracked 23,577,761 research outputs across all sources so far. Compared to these this one has done particularly well and is in the 97th percentile: it's in the top 5% of all research outputs ever tracked by Altmetric.
So far Altmetric has tracked 92,664 research outputs from this source. They typically receive a lot more attention than average, with a mean Attention Score of 100.5. This one has done well, scoring higher than 75% of its peers.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 246,287 tracked outputs that were published within six weeks on either side of this one in any source. This one has done particularly well, scoring higher than 97% of its contemporaries.
We're also able to compare this research output to 1,006 others from the same source and published within six weeks on either side of this one. This one has gotten more attention than average, scoring higher than 54% of its contemporaries.