The preparation of (-)-grandisine B from (+)-grandisine D; a biomimetic total synthesis or formation of an isolation artefact?
| Autor: | Cuthbertson JD; Department of Chemistry, University of York, Heslington, York YO10 5DD, UK., Godfrey AA, Taylor RJ |
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| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2011 Aug 05; Vol. 13 (15), pp. 3976-9. Date of Electronic Publication: 2011 Jun 30. |
| DOI: | 10.1021/ol2014939 |
| Abstrakt: | An efficient new alkyne-acetal cyclization procedure has been developed to prepare enantiopure indolizidine building blocks from l-proline and then applied to prepare the Elaeocarpus-derived alkaloids grandisine B and grandisine D in an efficient manner. However, evidence is presented which indicates that grandisine B does not occur naturally but is formed by reaction of grandisine D with ammonia during the extraction/purification process. (© 2011 American Chemical Society) |
| Databáze: | MEDLINE |
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