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

共 50 条

[31] Total synthesis and absolute configuration of koshikalide
Kunifuda, Kazuki
Iwasaki, Arihiro
Nagamoto, Masashi
Suenaga, Kiyotake
TETRAHEDRON LETTERS, 2016, 57 (29) : 3121 - 3123
[32] Total Synthesis and Absolute Configuration of (-)-Berkeleyamide A
Sperry, Jonathan
Harris, Eric B. J.
Brimble, Margaret A.
ORGANIC LETTERS, 2010, 12 (03) : 420 - 423
[33] Total synthesis and absolute configuration of polycavernoside A
Fujiwara, K
Murai, A
Yotsu-Yamashita, M
Yasumoto, T
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (41) : 10770 - 10771
[34] Total synthesis and absolute configuration of (-)-sedacryptine
Akiyama, E
Hirama, M
SYNLETT, 1996, (01) : 100 - &
[35] The absolute configuration and total synthesis of korormicin
Uehara, H
Oishi, T
Yoshikawa, K
Mochida, K
Hirama, M
TETRAHEDRON LETTERS, 1999, 40 (49) : 8641 - 8645
[36] Vanchrobactin:: absolute configuration and total synthesis
Soengas, Raquel G.
Anta, Cristina
Espada, Alfonso
Nieto, Rosa M.
Larrosa, Marta
Rodriguez, Jaime
Jimenez, Carlos
TETRAHEDRON LETTERS, 2007, 48 (17) : 3021 - 3024
[37] Total Synthesis of (-)-Fusarisetin A and Reassignment of the Absolute Configuration of Its Natural Counterpart
Deng, Jun
Zhu, Bo
Lu, Zhaoyong
Yu, Haixin
Li, Ang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) : 920 - 923
[38] Total synthesis of the coccinellid alkaloid (-)-adalinine and the assignment of its absolute configuration
Yamazaki, N
Ito, T
Kibayashi, C
TETRAHEDRON LETTERS, 1999, 40 (04) : 739 - 742
[39] Total synthesis of the proposed structure for pochonicine and determination of its absolute configuration
Kitamura, Yujiro
Koshino, Hiroyuki
Nakamura, Takemichi
Tsuchida, Aya
Nitoda, Teruhiko
Kanzaki, Hiroshi
Matsuoka, Koji
Takahashi, Shunya
TETRAHEDRON LETTERS, 2013, 54 (11) : 1456 - 1459
[40] STEREOSPECIFIC TOTAL SYNTHESIS OF (-)-KJELLMANIANONE AND A REVISION OF ITS ABSOLUTE-CONFIGURATION
ZHU, J
KLUNDER, AJH
ZWANENBURG, B
TETRAHEDRON LETTERS, 1994, 35 (17) : 2787 - 2790

← 1 2 3 4 5 →