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 language | English (US) |
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Pages (from-to) | 3713-3717 |
Number of pages | 5 |
Journal | Tetrahedron |
Volume | 72 |
Issue number | 26 |
DOIs | |
State | Published - Jun 30 2016 |
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Biochemistry
- Organic Chemistry
Keywords
- 1,4-Addition
- Conjugate addition
- Hydrindanone
- Linchpin
- Michael reaction
- Olefin cross metathesis