The cis-hydrindane motif (bicycle[4.3.0]nonane) is a common substructure in many natural products. A copper-catalyzed intermolecular Michael addition of silyl ketene ketal to beta-substituted alpha-alkoxycarbonyl-cyclopenetone was used to build a quaternary stereocenter; after incorporating another Michael acceptor motif into the system, the nucleophile beta-keto ester domain was able to undergo a metal-free intramolecular Michael reaction, giving substituted bicyclic cis-hydrindanone ring system with three continguous stereocenters. A leaving group could be incorporated into the Michael acceptor motif to serve as a �Lawton reagent� motif; in this case, the Michael addition would be followed with elimination, resulting cis-hydrindanones with an interesting alpha,beta-unsaturated carbonyl domain.

Diastereoselective synthesis of substituted <i>cis</i>-hydrindanones featuring sequential inter- and intramolecular Michael reactions

244th National Meeting (2012)

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Diastereoselective synthesis of substituted cis-hydrindanones featuring sequential inter- and intramolecular Michael reactions