Synthesis of Cyclobuta[<i>cd</i>]pentalenes via an Intramolecular Double Michael Addition Reaction of 1,3-Cyclopentanedione Derivatives
We describe an intramolecular double Michael addition reaction using 1,3-cyclopentanediones with a Michael acceptor at the C3' position of the C2 side chain through the formal umpolung of the 1,3-cyclopentanedione moiety. Silylation of the reactants generates 1,4-bis(silyloxy)cyclopentadienes, a silyloxy-substituted carbon which attacks the Michael acceptor to afford bicyclic scaffolds. Appropriate selection of the Michael acceptor induces further cyclization toward the activated cyclopentenone moiety to form a cyclobutane ring, affording cyclobuta[<i>cd</i>]pentalenes.
Authors
- Naoki Kanoh (ORCID: https://orcid.org/0000-0002-4382-3715)
- Masato Ono
- Kazutada Ikeuchi (ORCID: https://orcid.org/0000-0001-5343-3502)
- Takahiro Suzuki (ORCID: https://orcid.org/0000-0002-3842-1025)
- Tomonari Sasage
- Seiichi Nakamura (ORCID: https://orcid.org/0000-0001-9174-7895)
- Makoto Kobayashi (ORCID: https://orcid.org/0000-0003-0920-2154)
- Y. YAMAZAKI
- Keiji Tanino (ORCID: https://orcid.org/0000-0002-0580-0125)
Institutions
- Hokkaido University (JP)
- Nagoya City University (JP)
- Hoshi University (JP)
- Institute of Medicinal Plant Development (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-10
- DOI
- https://doi.org/10.1021/acs.orglett.5c03049
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Hokkaido University
- Japan Society for the Promotion of Science