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

Junjia Liu, Maurice A. Marsini, T. Aaron Bedell, Paul J. Reider, Erik J. Sorensen

Research output: Contribution to journalArticle

2 Scopus citations

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 β-substituted-α-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 β-ketoester. This strategy affords stereoselective access to substituted bicyclic cis-hydrindanone ring systems containing up to three contiguous stereocenters.

Original languageEnglish (US)
Pages (from-to)3713-3717
Number of pages5
JournalTetrahedron
Volume72
Issue number26
DOIs
StatePublished - Jun 30 2016

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • 1,4-Addition
  • Conjugate addition
  • Hydrindanone
  • Linchpin
  • Michael reaction
  • Olefin cross metathesis

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