Diastereoselective SmI2 mediated cascade radical cyclisations of methylenecyclopropane derivatives - syntheses of paeonilactone B and 6-epi-paeonilactone A
Boffey, Raymond J., Whittingham, William G. and Kilburn, Jeremy D. (2001) Diastereoselective SmI2 mediated cascade radical cyclisations of methylenecyclopropane derivatives - syntheses of paeonilactone B and 6-epi-paeonilactone A. Journal of the Chemical Society, Perkin Transactions 1, (5), 487-496. (doi: 10.1039/b009513n)
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Official URL: http://dx.doi.org/10.1039/b009513n
Description/Abstract
The SmI2 mediated cascade cyclisations of several methylenecyclopropyl ketones have been examined and found to proceed with high diastereoselectivity, which is critically dependent on the presence of HMPA in the reaction. In one case the radical species at the end of the cascade sequence underwent an unexpected and highly stereoselective dimerisation. The cascade methodology has been applied to a short synthesis of (+/-)-paeonilactone B and of (+/-)-6-epi-paeonilactone A.
| Item Type: | Article |
|---|---|
| ISSN: | 0300-922 (print) |
| Uncontrolled Keywords: | divalent lanthanide derivatives, samarium(ii) iodide, organic-synthesis, stereoselective synthesis, cyclization reactions, acyclic precursors, r-(-)-carvone, dimerization, sequence, systems |
| Related URLs: | http://dx.doi.org/10.1039/b009513n |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| ePrint ID: | 19414 |
| URI: | http://eprints.soton.ac.uk/id/eprint/19414 |
| Deposited On: | 14 Feb 2006 |
| Last Modified: | 01 Apr 2012 01:55 |
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