التفاصيل البيبلوغرافية
| العنوان: |
Total Synthesis of Diverse Tetramic Acid Bearing cis‐Decalin Natural Products. |
| المؤلفون: |
Dong, Haoran1 (AUTHOR), Hu, Dachao2 (AUTHOR), Hong, Benke1 (AUTHOR), Wang, Jin1 (AUTHOR), Lei, Xiaoguang1,3 (AUTHOR) xglei@pku.edu.cn |
| المصدر: |
Angewandte Chemie International Edition. 5/8/2023, Vol. 62 Issue 20, p1-6. 6p. |
| مصطلحات موضوعية: |
*TETRAMIC acids, *NATURAL products, *ACID derivatives, *DIELS-Alder reaction, *EPOXY resins, *ACIDS |
| مستخلص: |
We report herein the first total syntheses of four natural antibiotics, vermisporin, PF1052/AB4015‐A, AB4015‐L, AB4015‐B, and one hydrogenated natural product derivative, AB4015‐A2, that all feature a tetramic acid bearing cis‐decalin ring. The construction of the functionalized cis‐decalin ring was achieved by a diastereoselective intramolecular Diels‐Alder (IMDA) reaction, which proceeded via a rare endo‐boat transition state. Through an intramolecular neighboring‐group‐oriented strategy, the sterically hindered epoxy group in vermisporin, PF1052/AB4015‐A and AB4015‐L was installed efficiently. A one‐pot aminolysis/Dieckmann condensation cascade using l‐amino acid derivatives afforded the desired tetramic acid structure. The total synthesis led to the unambiguous verification of the absolute configuration of these natural products. [ABSTRACT FROM AUTHOR] |
| قاعدة البيانات: |
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