74173-20-9Relevant articles and documents
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.
supporting information; experimental part, p. 6862 - 6865 (2009/07/18)
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.
