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

ABSTRACT: The hydrindane (bicyclo[4.3.0]nonane) structural motif (1) and related cis-1-hydrindanone skeleton (2) are common substructures in many natural products. Herein, we describe efficient access to substituted cis-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 cis-hydrindanone ring systems containing up to three contiguous stereocenters.

SUBMITTER: Liu J 

PROVIDER: S-EPMC5021295 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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

Liu Junjia J   Marsini Maurice A MA   Bedell T Aaron TA   Reider Paul J PJ   Sorensen Erik J EJ  

Tetrahedron 20160315 26

The hydrindane (bicyclo[4.3.0]nonane) structural motif (<b>1</b>) and related <i>cis</i>-1-hydrindanone skeleton (<b>2</b>) are common substructures in many natural products. Herein, we describe efficient access to substituted <i>cis</i>-1-hydrindanones enabled by a sequence of Michael reactions. A copper-catalyzed intermolecular Michael addition of a cyclic silyl ketene acetal to a <i>β</i>-substituted-<i>α</i>-alkoxycarbonyl-cyclopentenone enables construction of a quaternary center and is fol  ...[more]

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