Total Synthesis of Sophoraflavanone H and Confirmation of Its Absolute Configuration

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 diast...

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Bibliographic Details
Published in:Organic letters 2020-05, Vol.22 (10), p.3820-3824
Main Authors: Murakami, Haruka, Asakawa, Tomohiro, Muramatsu, Yoshihiro, Ishikawa, Ryo, Hiza, Aiki, Tsukaguchi, Yuta, Tokumaru, Yohei, Egi, Masahiro, Inai, Makoto, Ouchi, Hitoshi, Yoshimura, Fumihiko, Taniguchi, Tohru, Ishikawa, Yoshinobu, Kondo, Mitsuru, Kan, Toshiyuki
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01063