Construction of the Tetracyclic Skeleton of Polycyclic Norcembranoids Sinudenoids B–D Via Ireland-Claisen Rearrangement
Sinudenoids B-D represent a biologically significant and structurally intricate family of natural products distinguished by their unique [5-5-6-6] tetracyclic skeleton. Herein, we present an efficient strategy for the asymmetric synthesis of their [5-5-6-6] tetracyclic framework. Key features of our approach include a convergent synthetic strategy driven by esterification, a pivotal Ireland-Claisen rearrangement to construct a C11-C12 bond, followed by efficient lactonization and isomerization, and a ring-closing metathesis to complete the [5-5-6-6] tetracyclic skeleton.
Authors
- Xingang Xie (ORCID: https://orcid.org/0000-0002-0707-1229)
- Hui Shen (ORCID: https://orcid.org/0000-0003-0335-6064)
- Xiaofei Gao (ORCID: https://orcid.org/0000-0003-2799-7421)
- Gaoyuan Zhao (ORCID: https://orcid.org/0000-0003-4838-865X)
- Liang Huo
- Peng Chen (ORCID: https://orcid.org/0000-0002-6252-5772)
- Huilin Li (ORCID: https://orcid.org/0000-0001-8088-6718)
- Xuegong She (ORCID: https://orcid.org/0000-0002-3002-2433)
Institutions
- Lanzhou University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-03-20
- DOI
- https://doi.org/10.1021/acs.joc.5c00317
- Citations
- 2
- Primary Topic
- Marine Sponges and Natural Products
- Type
- article
- Field-Weighted Citation Impact
- 2.47
Funders
- National Natural Science Foundation of China
- Fundamental Research Funds for the Central Universities
- Science and Technology Program of Gansu Province