Total Syntheses of β‐ and γ‐Naphthocyclinones
After half a century from their isolation in 1974, we report the first total syntheses of β- and γ-naphthocyclinones, two dimeric pyranonaphthoquinones featuring an unusual bicyclo[3.2.1]octadienone core. The syntheses were achieved with full stereochemical control and functional group management, relying on 1) enantioselective construction of the bicyclic core by Rh-catalyzed enantioselective 1,4-addition followed by thiolate-mediated reductive cyclization, and 2) judicious design of a common chiral, non-racemic monomer unit that is capable of divergence into the donor and acceptor units, and reunion to construct the bicyclo[3.2.1]octadienone core.
Authors
- Keisuke Suzuki (ORCID: https://orcid.org/0000-0001-7935-3762)
- Mark M. Maturi (ORCID: https://orcid.org/0000-0002-4145-6982)
- Ken Ohmori (ORCID: https://orcid.org/0000-0002-8498-0821)
- Yoshio Ando (ORCID: https://orcid.org/0000-0002-0063-7672)
- Takumi Fukazawa
- Nozomi Tanaka (ORCID: https://orcid.org/0000-0003-3910-3659)
- Yusuke Nakazawa (ORCID: https://orcid.org/0000-0001-9817-2684)
- Taiju Hoshino
Institutions
- Tokyo Institute of Technology (JP)
- Suzuki (Japan) (JP)
- Kitasato Institute Hospital (JP)
- Institute of Science Tokyo (JP)
- Kitasato University (JP)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2024-10-10
- DOI
- https://doi.org/10.1002/anie.202415108
- Citations
- 6
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 1.50
Funders
- Takeda Science Foundation
- TOBE MAKI Scholarship Foundation
- Japan Society for the Promotion of Science