Total Synthesis of Sophoraflavanone H and Confirmation of Its Absolute Configuration

被引：5

作者：

Murakami, Haruka ^{[1
]}

Asakawa, Tomohiro ^{[1
,2
]}

Muramatsu, Yoshihiro ^{[1
]}

Ishikawa, Ryo ^{[1
]}

Hiza, Aiki ^{[1
]}

Tsukaguchi, Yuta ^{[1
]}

Tokumaru, Yohei ^{[1
]}

Egi, Masahiro ^{[1
]}

Inai, Makoto ^{[1
]}

Ouchi, Hitoshi ^{[1
]}

Yoshimura, Fumihiko ^{[1
]}

Taniguchi, Tohru ^{[3
]}

Ishikawa, Yoshinobu ^{[1
]}

Kondo, Mitsuru ^{[4
]}

Kan, Toshiyuki ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Shizuoka, Shizuoka 4228526, Japan

[2] Tokai Univ, Dept Fisheries Food Sci, Shizuoka 4248610, Japan

[3] Hokkaido Univ, Fac Adv Life Sci, Frontier Res Ctr Adv Mat & Life Sci, Sapporo, Hokkaido 0010021, Japan

[4] Shizuoka Univ, Grad Sch Sci & Technol, Shizuoka, Shizuoka 4228529, Japan

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 10期

关键词：

STEREOCONTROLLED TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC-SYNTHESIS; INSERTION;

D O I：

10.1021/acs.orglett.0c01063

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3820 / 3824

页数：5

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