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

ABSTRACT

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 ß-diketone, intramolecular cyclization, and Suzuki-Miyaura coupling to achieve the subunit diene.