Asymmetric Total Synthesis of (−)-Plicatic Acid via a Highly Enantioselective and Diastereoselective Nucleophilic Epoxidation of Acyclic Trisubstitued Olefins
Published in
Journal of the American Chemical Society, July 2009
The first total synthesis of (-)-plicatic acid has been achieved by a concise and enantioselective route. In this synthesis, a conceptually new strategy featuring an asymmetric epoxidation-intramolecular epoxy-ring-opening Friedel-Crafts reaction sequence was developed for the stereoselective construction of the 2,7'-cyclolignane skeleton bearing contiguous quaternary-quaternary-tertiary stereocenters. The implementation of this strategy was enabled by the development of a modified protocol for the Seebach epoxidation with TADOOH, which affords an unprecedented, highly enantioselective and diastereoselective epoxidation with a range of alpha-carbonyl-beta-substituted acrylates 3.
Pharmacology, Toxicology and Pharmaceutical Science
1
3%
Physics and Astronomy
1
3%
Unknown
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18%
Attention Score in Context
Attention Score in Context
This research output has an Altmetric Attention Score of 11. 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 16 September 2026.
All research outputs
#4,248,884
of 34,344,963 outputs
Outputs from Journal of the American Chemical Society
#15,107
of 90,199 outputs
Outputs of similar age
#18,545
of 173,350 outputs
Outputs of similar age from Journal of the American Chemical Society
#81
of 440 outputs
Altmetric has tracked 34,344,963 research outputs across all sources so far. Compared to these this one has done well and is in the 87th percentile: it's in the top 25% of all research outputs ever tracked by Altmetric.
So far Altmetric has tracked 90,199 research outputs from this source. They typically receive more attention than average, with a mean Attention Score of 7.8. This one has done well, scoring higher than 82% 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 173,350 tracked outputs that were published within six weeks on either side of this one in any source. This one has done well, scoring higher than 88% of its contemporaries.
We're also able to compare this research output to 440 others from the same source and published within six weeks on either side of this one. This one has done well, scoring higher than 81% of its contemporaries.
