Abstract
The first total synthesis of two possible diastereomers of natural 6-chlorotetrahydrofuran acetogenin 1 has been achieved. The synthetic route features 5-exo-tet cyclization, Z selective Wittig reaction and Julia olefination for the construction of conjugated diene and enyne moieties, and stereoselective chlorination. Comparison of their 1H and 13C NMR data and specific rotation with those of the natural product elucidated the absolute configuration of natural (−)-6-chlorotetrahydrofuran acetogenin 1.
| Original language | English |
|---|---|
| Pages (from-to) | 17191-17194 |
| Number of pages | 4 |
| Journal | Chemistry - A European Journal |
| Volume | 23 |
| Issue number | 68 |
| DOIs | |
| Publication status | Published - Dec 6 2017 |
Keywords
- natural products
- stereoselective synthesis
- structure elucidation
- tetrahydrofuran
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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Takamura, H., Katsube, T., Okamoto, K., & Kadota, I. (2017). Total Synthesis of Two Possible Diastereomers of Natural 6-Chlorotetrahydrofuran Acetogenin and Its Stereostructural Elucidation. Chemistry - A European Journal, 23(68), 17191-17194. https://doi.org/10.1002/chem.201703234