| Title |
Synthesis of (−)‐Morphine: Application of Sequential Claisen/Claisen Rearrangement of an Allylic Vicinal Diol
|
|---|---|
| Published in |
Chemistry - A European Journal, November 2012
|
| DOI | 10.1002/chem.201203284 |
| Pubmed ID | |
| Authors |
Masato Ichiki, Hiroki Tanimoto, Shohei Miwa, Ryosuke Saito, Takaaki Sato, Noritaka Chida |
| Abstract |
A detailed exploration of the synthesis of (-)-morphine based on sequential [3,3]-sigmatropic rearrangements is described. The sequential Claisen/Claisen rearrangements of an allylic vicinal diol resulted in the stereoselective formation of the two contiguous carbon centers, including a sterically encumbered quaternary carbon, in a single operation. The two ethyl esters generated in this reaction were successfully differentiated during a subsequent Friedel-Crafts-type cyclization. The (-)-morphine double bond was introduced at a late stage in our first-generation synthesis, but was formed at an earlier stage in the second-generation synthesis, resulting in a more efficient route to the end product. |
Mendeley readers
The data shown below were compiled from readership statistics for 42 Mendeley readers of this research output. Click here to see the associated Mendeley record.
Geographical breakdown
| Country | Count | As % |
|---|---|---|
| United States | 1 | 2% |
| Unknown | 41 | 98% |
Demographic breakdown
| Readers by professional status | Count | As % |
|---|---|---|
| Student > Ph. D. Student | 7 | 17% |
| Student > Bachelor | 5 | 12% |
| Student > Doctoral Student | 3 | 7% |
| Researcher | 3 | 7% |
| Student > Postgraduate | 3 | 7% |
| Other | 9 | 21% |
| Unknown | 12 | 29% |
| Readers by discipline | Count | As % |
|---|---|---|
| Chemistry | 24 | 57% |
| Unspecified | 2 | 5% |
| Engineering | 2 | 5% |
| Medicine and Dentistry | 1 | 2% |
| Computer Science | 1 | 2% |
| Other | 0 | 0% |
| Unknown | 12 | 29% |
Attention Score in Context
This research output has an Altmetric Attention Score of 6. 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 03 April 2017.
All research outputs
#6,351,872
of 24,633,436 outputs
Outputs from Chemistry - A European Journal
#5,253
of 22,969 outputs
Outputs of similar age
#62,026
of 286,440 outputs
Outputs of similar age from Chemistry - A European Journal
#45
of 142 outputs
Altmetric has tracked 24,633,436 research outputs across all sources so far. This one has received more attention than most of these and is in the 73rd percentile.
So far Altmetric has tracked 22,969 research outputs from this source. They receive a mean Attention Score of 3.9. This one has done well, scoring higher than 76% 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 286,440 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 78% of its contemporaries.
We're also able to compare this research output to 142 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 66% of its contemporaries.