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Total Synthesis of Sophoraflavanone H and Confirmation of Its Absolute Configuration.

Haruka MurakamiTomohiro AsakawaYoshihiro MuramatsuRyo IshikawaAiki HizaYuta TsukaguchiYohei TokumaruMasahiro EgiMakoto InaiHitoshi OuchiFumihiko YoshimuraTohru TaniguchiYoshinobu IshikawaMitsuru KondoToshiyuki Kan
Published in: Organic letters (2020)
Sophoraflavanone H (1) is a polyphenol with a hybrid-type structure containing 2,3-diaryl-2,3-dihydrobenzofuran and flavanone ring moieties. This compound and related analogues are promising leads for antimicrobial and antitumor drug development. Here we describe a total synthesis of 1 and its diastereomer. The dihydrobenzofuran and flavanone rings were constructed by a Rh-catalyzed asymmetric C-H insertion reaction and selective oxy-Michael reaction. The absolute configuration of 1 was established by X-ray crystallographic analysis and CD spectral investigation of synthetic derivatives.
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