Collective Biomimetic Synthesis of Myrcaulones A and C and Myrcauones B–D
We report the first collective biomimetic synthesis of noncanonical phloroglucinol derivatives myrcaulones A (<b>1</b>) and C (<b>3</b>), featuring a unique ring-contracted phloroglucinol skeleton, along with three biosynthetically related canonical phloroglucinol derivatives myrcauones B-D (<b>4</b>-<b>6</b>). These compounds were synthesized in only 6-9 steps, starting from the commercially available 3,4,5-trimethoxyphenol. Key features of the synthetic strategy include a <i>hetero</i>-Diels-Alder reaction to construct the canonical phloroglucinol framework and an α-ketol rearrangement-driven ring contraction reaction to form the noncanonical phloroglucinol skeleton.
Authors
- Lijun Hu (ORCID: https://orcid.org/0000-0002-3019-6548)
- Zizhe Cai (ORCID: https://orcid.org/0000-0002-7103-4975)
- Wen‐Cai Ye (ORCID: https://orcid.org/0000-0002-2810-1001)
- Ying Wang (ORCID: https://orcid.org/0000-0003-4524-1812)
- Yifan Liu (ORCID: https://orcid.org/0000-0003-3123-8903)
- Xiao‐Jun Huang (ORCID: https://orcid.org/0000-0002-3636-4813)
- Xiaoxia Chen (ORCID: https://orcid.org/0000-0002-1196-234X)
- Jian‐Guo Song (ORCID: https://orcid.org/0000-0003-3843-355X)
- Wang Fang (ORCID: https://orcid.org/0009-0006-6240-9671)
- Zhi‐Zhang Duan
- Zijian Peng
Institutions
- Jinan University (CN)
- Guangdong Pharmaceutical University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-06
- DOI
- https://doi.org/10.1021/acs.orglett.5c01758
- Citations
- 2
- Primary Topic
- Natural Compound Pharmacology Studies
- Type
- article
- Field-Weighted Citation Impact
- 3.50
Funders
- National Natural Science Foundation of China
- Guangzhou Municipal Science and Technology Project
- National Key Research and Development Program of China
- Basic and Applied Basic Research Foundation of Guangdong Province