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A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Wang, Ning Zhang, Li-He Ye, Xin-Shan |
| Copyright Year | 2010 |
| Abstract | A facile, versatile and stereoselective synthesis of bicyclic polyhydroxylated alkaloids as castanospermine analogues is described. The synthetic route started from methyl pyranosides. The key steps involved a high-yielding expeditious one-pot tandem reaction from alkenes to N-substituted delta-lactams. The delta-lactams were stereoselectively vinylated to give the dienes, which were followed by the ring-closing metathesis to produce the cyclized products. The functional group transformations of the resulting bicyclic compounds furnished diverse polyhydroxylated alkaloids in good yields. |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/b923180c |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/ob/b9/b923180c/b923180c.pdf |
| PubMed reference number | 20376396 |
| Alternate Webpage(s) | https://doi.org/10.1039/b923180c |
| Journal | Medline |
| Volume Number | 8 |
| Issue Number | 11 |
| Journal | Organic & biomolecular chemistry |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |