Discovery of the Nonenzymatic Formation of 3,3′-Spirooxindole γ-Butyrolactones Enables One-Step Construction of the Core Skeleton
Abstract 3,3′-Spirooxindole γ-butyrolactones are a small but intriguing family of natural products with diverse bioactivities and unique biosynthetic origins. Herein, we demonstrate that this core skeleton can form spontaneously via a nonenzymatic aldol condensation–lactonization cascade between 2-oxindole-3-acetic acid and aldehydes under mild conditions. Inspired by this biosynthetic insight, we developed an efficient method for the construction of the 3,3′-spirooxindole γ-butyrolactone scaffold, enabling the collective synthesis of seven natural products and broad structural diversification.
Authors
- Weiming Zhu (ORCID: https://orcid.org/0000-0002-7591-3264)
- Peng Fei Fu (ORCID: https://orcid.org/0000-0002-7768-4004)
- Chao Gao (ORCID: https://orcid.org/0000-0002-5205-0670)
- Zhi Liu (ORCID: https://orcid.org/0000-0002-1417-9852)
- Jingjing Shen (ORCID: https://orcid.org/0009-0000-0924-611X)
- Zhenbang Zhao
Institutions
- Qingdao National Laboratory for Marine Science and Technology (CN)
- Ocean University of China (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-10-30
- DOI
- https://doi.org/10.1021/acs.orglett.6c04315
- Primary Topic
- Synthesis of Indole Derivatives
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Shandong Province
- Taishan Scholar Project of Shandong Province
- Fundamental Research Funds for the Central Universities