Total Synthesis of Mulberry Diels-Alder-Type Adducts Kuwanons G and H.

Si-Yuan Luo, Zhuo-Ya Tang, Qingjiang Li, Jiang Weng, Sheng Yin, Gui-Hua Tang

The Journal of organic chemistry 2021 Mar 19

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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.

Citation

Si-Yuan Luo, Zhuo-Ya Tang, Qingjiang Li, Jiang Weng, Sheng Yin, Gui-Hua Tang. Total Synthesis of Mulberry Diels-Alder-Type Adducts Kuwanons G and H. The Journal of organic chemistry. 2021 Mar 19;86(6):4786-4793