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Inter- and intramolecular reactions of 1-deoxy-1-thio-1,6-anhydrosugars with α-diazoesters: synthesis of the tagetitoxin core by photochemical ylide rearrangement.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Mortimer, Anne J. Price Plet, Julien Rene-Hubert Obasanjo, Oluwafunsho A. Kaltsoyannis, Nikolas Porter, Michael J. |
| Copyright Year | 2012 |
| Abstract | The one-carbon ring expansion of 1-deoxy-1-thio-1,6-anhydrosugars, mediated by metal carbenes and proceeding through the intermediacy of sulfur ylides, has been proposed as a route for the synthesis of the tagetitoxin skeleton. Intermolecular reactions of such thioanhydrosugars with diazoesters afford a range of undesired products derived from the initially formed ylide, whereas use of an intramolecular process generates stable ylides which can be converted to the tagetitoxin skeleton by photo-Stevens rearrangement. Computational studies using density functional theory indicate that the photochemical rearrangement likely proceeds through a homolysis-recombination pathway. |
| Starting Page | 311 |
| Ending Page | 317 |
| Page Count | 7 |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/ob/c2/c2ob26308d/c2ob26308d.pdf |
| PubMed reference number | 22965829v1 |
| Alternate Webpage(s) | https://doi.org/10.1039/c2ob26308d |
| DOI | 10.1039/c2ob26308d |
| Journal | Organic & biomolecular chemistry |
| Volume Number | 10 |
| Issue Number | 43 |
| Language | English |
| Access Restriction | Open |
| Subject Keyword | DNA Sequence Rearrangement Technetium Tc 99m Sulfur Colloid carbene tagetitoxin ylide |
| Content Type | Text |
| Resource Type | Article |
