Reinvestigation of the Synthesis of Isoliquiritigenin: Application of Horner-Wadsworth-Emmons Reaction and Claisen-Schmidt Condensation

被引：8

作者：

Sano, Shigeki ^{[1
]}

Okubo, Yoshinori ^{[1
]}

Handa, Atsushi ^{[1
]}

Nakao, Michiyasu ^{[1
]}

Kitaike, Syuji ^{[1
]}

Nagao, Yoshimitsu ^{[1
]}

Kakegawa, Hisao ^{[2
]}

机构：

[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan

[2] Kagawa Univ, Fac Engn, Kagawa 7610396, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2011年 / 59卷 / 07期

关键词：

isoliquiritigenin; chalcone; Horner-Wadsworth-Emmons reaction; Claisen-Schmidt condensation; cis-trans isomerization; PROSTATE-CANCER; CELLS; DERIVATIVES; EXPRESSION; FLAVONOIDS; CATALYST;

D O I：

10.1248/cpb.59.885

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Isoliquiritigenin [ILG, (E)-1] was readily prepared via the Horner-Wadsworth-Emmons reactions using beta-ketophosphonates 5a, b. An improved protocol for the synthesis of (E)-1 via the Claisen-Schmidt condensation was also presented.

引用

页码：885 / 888

页数：4

共 50 条

[31] Applications of the Horner-Wadsworth-Emmons Olefination in Modern Natural Product Synthesis
Roman, David
Sauer, Maria
Beemelmanns, Christine
SYNTHESIS-STUTTGART, 2021, 53 (16): : 2713 - 2739
[32] SYNTHESIS OF POLYCONJUGATED ALDEHYDES USING A NEW HORNER-WADSWORTH-EMMONS REAGENT
REIN, T
AKERMARK, B
HELQUIST, P
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1988, 42 (08): : 569 - 572
[33] Synthesis of the Sulfonate Analogue of Seminolipid via Horner-Wadsworth-Emmons Olefination
Franchini, Laura
Compostella, Federica
Colombo, Diego
Panza, Luigi
Ronchetti, Fiamma
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15): : 5363 - 5366
[34] Synthesis of unsaturated organotrifluoroborates via Wittig and Horner-Wadsworth-Emmons olefination
Molander, Gary A.
Figueroa, Ruth
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16): : 6135 - 6140
[35] A Novel and Convenient Synthesis of Cyclopent-1-enecarboxylates by an Intramolecular Horner-Wadsworth-Emmons Reaction
Krawczyk, Henryk
Albrecht, Lukasz
SYNTHESIS-STUTTGART, 2008, (24): : 3951 - 3956
[36] Quantum mechanical investigation of the Horner-Wadsworth-Emmons reaction of benzyl pyridyl ketone
Kim, Jinyoung
Park, Kwang-Su
Yeo, Woon-Seok
Chong, Youhoon
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2008, 29 (06) : 1269 - 1272
[37] Efficient synthesis of α,β-unsaturated ketones with trans-selective Horner-Wadsworth-Emmons reaction in water
Jafari, Abbas Ali
Ghadami, Mahboobeh
ENVIRONMENTAL CHEMISTRY LETTERS, 2016, 14 (02) : 223 - 228
[38] Highly Z-selective synthesis of α,β-unsaturated nitriles using the Horner-Wadsworth-Emmons reaction
Ando, Kaori
Okumura, Miho
Nagaya, Shigeo
TETRAHEDRON LETTERS, 2013, 54 (15) : 2026 - 2028
[39] Chain-Growth Horner-Wadsworth-Emmons Condensation Polymerization Initiated with an Aliphatic Aldehyde
Sato, Keichiro
Goto, Eisuke
Ochiai, Yuto
Higashihara, Tomoya
JOURNAL OF PHOTOPOLYMER SCIENCE AND TECHNOLOGY, 2019, 32 (01) : 73 - 76
[40] A facile method for the stereoselective Horner-Wadsworth-Emmons reaction of aryl alkyl ketones
Sano, S
Yokoyama, K
Shiro, M
Nagao, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (05) : 706 - 709

← 1 2 3 4 5 →