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Diastereoselective SmI2 mediated cascade radical cyclisations of methylenecyclopropane derivatives — syntheses of paeonilactone B and 6-epi-paeonilactone A

Authors :
Raymond John Boffey
William Guy Whittingham
Jeremy D. Kilburn
Source :
Journal of the Chemical Society, Perkin Transactions 1. :487-496
Publication Year :
2001
Publisher :
Royal Society of Chemistry (RSC), 2001.

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.

Details

ISSN :
13645463 and 14727781
Database :
OpenAIRE
Journal :
Journal of the Chemical Society, Perkin Transactions 1
Accession number :
edsair.doi...........d3d2fca809ce994dee54d6acf96a3693
Full Text :
https://doi.org/10.1039/b009513n