Total Synthesis of Mulberry Diels–Alder-Type Adducts Kuwanons G and H
| Autor: | Zhuo-Ya Tang, Qingjiang Li, Sheng Yin, Si-Yuan Luo, Gui-Hua Tang, Jiang Weng |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Cycloaddition Reaction
Diene 010405 organic chemistry Stereochemistry Protein subunit Organic Chemistry Intramolecular cyclization Total synthesis Alkylation 010402 general chemistry 01 natural sciences 0104 chemical sciences Adduct chemistry.chemical_compound Chalcones chemistry Cyclization Polyphenol Fruit Diels alder Morus |
| Zdroj: | The Journal of Organic Chemistry. 86:4786-4793 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | Mulberry Diels-Alder-type adducts (MDAAs) are a group of rare natural polyphenols biosynthetically derived from [4 + 2]-cycloaddition of chalcones and dehydroprenylphenols. In this study, kuwanons G (1) and H (2), two bioactive MDAAs with unique dehydroprenylflavonoid dienes, were totally synthesized for the first time in a biomimetic manner. The key features of the convergent route include the use of the Baker-Venkataraman rearrangement, alkylation of β-diketone, intramolecular cyclization, and Suzuki-Miyaura coupling to achieve the subunit diene. |
| Databáze: | OpenAIRE |
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