The hydrindane (bicyclo[4.3.0]nonane) structural motif () and related -1-hydrindanone skeleton () are common substructures in many natural products. Herein, we describe efficient access to substituted -1-hydrindanones enabled by a sequence of Michael reactions. A copper-catalyzed intermolecular Michael addition of a cyclic silyl ketene acetal to a -substituted--alkoxycarbonyl-cyclopentenone enables construction of a quaternary center and is followed, after incorporation of an additional Michael acceptor, by a second, intramolecular addition of a nucleophilic -ketoester. This strategy affords stereoselective access to substituted bicyclic -hydrindanone ring systems containing up to three contiguous stereocenters.
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| http://dx.doi.org/10.1016/j.tet.2016.03.039 | DOI Listing |
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