Concise total synthesis of biologically interesting pyranochalcone natural products: Citrunobin, boesenbergin A, boesenbergin B, xanthohumol C, and glabrachromene

被引：54

作者：

Lee, Yong Rok ^{[1
]}

Xia, Likai ^{[1
]}

机构：

[1] Yeungnam Univ, Sch Chem Engn & Technol, Kyongsan 712749, South Korea

来源：

SYNTHESIS-STUTTGART | 2007年 / 20期

关键词：

pyranochalcone; citrunobin; boesenbergins A and B; xanthohumol C; glabrachromene;

D O I：

10.1055/s-2007-990796

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New and efficient synthetic approaches to the biologically interesting natural products citrunobin, boesenbergins A and B, xanthohumol C, and glabrachromene are described. The key strategies involve ethylenediamine diacetate catalyzed benzopyran formation reactions and base-catalyzed aldol reactions.

引用

页码：3240 / 3246

页数：7

共 44 条

[1] Continuous processing to control a potentially hazardous process:: Conversion of aryl 1,1-dimethylpropargyl ethers to 2,2-dimethylchromenes (2,2-dimethyl-2H-1-benzopyrans) [J].

Bogaert-Alvarez, RJ ;

Demena, P ;

Kodersha, G ;

Polomski, RE ;

Soundararajan, N ;

Wang, SSY .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (06) :636-645

[2] A one-pot synthesis of functionalized 2,2-disubstituted 2H-1-benzopyrans [J].

Cossy, J ;

Rakotoarisoa, H ;

Kahn, P ;

Desmurs, JR .

TETRAHEDRON LETTERS, 1998, 39 (52) :9671-9674

[3] PRENYLATED DIBENZOYLMETHANE DERIVATIVES FROM THE ROOT OF GLYCYRRHIZA-INFLATA (XINJIANG LICORICE) [J].

DEMIZU, S ;

KAJIYAMA, K ;

HIRAGA, Y ;

KINOSHITA, K ;

KOYAMA, K ;

TAKAHASHI, K ;

TAMURA, Y ;

OKADA, K ;

KINOSHITA, T .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (02) :392-395

[4] New bioactive flavonoids and stilbenes in cube resin insecticide [J].

Fang, NB ;

Casida, JE .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (02) :205-210

[5] PALLADIUM CATALYZED SYNTHESIS OF CHROMENES AND CHROMENOLS [J].

GARCIAS, X ;

BALLESTER, P ;

SAA, JM .

TETRAHEDRON LETTERS, 1991, 32 (52) :7739-7742

[6]

Gerhauser C, 2002, MOL CANCER THER, V1, P959

[7] Synthesis of various 2H-benzopyran compounds and their kinetic resolution by asymmetric hydrolysis of their racemic acetates mediated by lipases [J].

Goujon, JY ;

Zammattio, F ;

Kirschleger, B .

TETRAHEDRON-ASYMMETRY, 2000, 11 (11) :2409-2420

[8]

Gripenberg J., 1962, CHEM FLAVONOID COMPO, P409

[9] Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production [J].

Han, AR ;

Kang, YJ ;

Windono, T ;

Lee, SK ;

Seo, EK .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (04) :719-721

[10]

Harborne J. B., 1999, HDB NATURAL FLAVONOI, P1

← 1 2 3 4 5 →