87994-96-5Relevant academic research and scientific papers
A flexible, stereoselective approach to the decorated cis-hydrindane skeleton: Synthesis of the proposed structure of faurinone
Findley, Thomas J. K.,Sucunza, David,Miller, Laura C.,Davies, David T.,Procter, David J.
, p. 6862 - 6865 (2008)
A flexible, stereoselective approach to the cis-hydrindane motif found in a number of biologically active natural products that utilizes highly diastereoselective SmI2-mediated cyclizations of aldehyde and halide substrates was demonstrated. Aldehydes were prepared to investigate the stereoselectivity of the proposed SmI2-mediated construction of the cis-hydrindane system. Treatment of aldehydes with SmI2 in THF and tBuOH resulted in successful cyclization and construction of three contiguous stereocenters. This cyclization proceeds through reduction of the aldehyde and addition of the resulting ketyl-radical anion to the alkene through anti-transition structure to give samarium (III) enolates. It was observed that SmI2-mediated halide-alkene cyclizations provide an easy alternative for the synthesis of less oxygenated targets.
A stereoselective, Sm(ii)-mediated approach to decorated cis-hydrindanes: Synthetic studies on faurinone and pleuromutilin
Findley, Thomas J. K.,Sucunza, David,Miller, Laura C.,Helm, Matthew D.,Helliwell, Madeleine,Davies, David T.,Procter, David J.
scheme or table, p. 2433 - 2451 (2011/05/06)
The cis-hydrindane motif is found in a number of natural products that display important biological activity. A flexible, stereoselective approach to the framework has been developed that features highly diastereoselective, SmI2-mediated cyclisations. The strategy has been exploited in the first synthesis of the proposed structure of faurinone and an approach to the skeleton of the antibacterial natural product, pleuromutilin.
