Total Synthesis of Racemic Benzosceptrins via an Electrocyclization Cascade
Benzosceptrins are dimeric pyrrole-2-aminoimidazole alkaloids isolated from marine sponges of the genus <i>Agelas</i>, and they are characterized by the <i>C</i><sub>2</sub> symmetric benzocyclobutane structure. Here, we report the total synthesis of (±)-benzosceptrins A, B, and C via sequential 8π and 6π electrocyclizations of nagelamide I and its structurally related analogues based on a Gibbs energy evaluation of the proposed biosynthetic pathway.
Authors
- Keisuke Fukaya (ORCID: https://orcid.org/0000-0002-7148-4714)
- Daisuke Urabe (ORCID: https://orcid.org/0000-0002-1999-9374)
- Kei Fukuyama (ORCID: https://orcid.org/0000-0002-6058-3362)
- Taisei Matoba
- Kazuki Saito (ORCID: https://orcid.org/0000-0003-4663-1134)
- A. Amano
- Yudai Fujino
Institutions
- Toyama Institute of Health (JP)
- Toyama Prefectural University (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-11-26
- DOI
- https://doi.org/10.1021/acs.orglett.5c04155
- Primary Topic
- Marine Sponges and Natural Products
- Type
- article
- Field-Weighted Citation Impact
- 0.00