Total syntheses of three natural products, vignafuran, 2-(4-hydroxy-2-methoxyphenyl)-6-methoxybenzofuran-3-carboxylic acid methyl ester, and coumestrol from a common starting material

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作者：

Grad. Sch. of Pharmaceutical Sci., Tohoku University, Aoba-ku, Sendai 980-8578, Japan ^{[1
]}

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来源：

Journal of the Chemical Society, Perkin Transactions 1 | 2000年 / 24期

关键词：

Carbonylation - Catalysis - Column chromatography - Complexation - Hydrolysis - Palladium compounds - Synthesis (chemical);

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摘要：

Vignafuran, 2-(4-hydroxy-2-methoxyphenyl)-6-methoxybenzofuran-3-carboxylic acid methyl ester, and coumestrol were synthesized from a common starting material. Reaction step involved in the synthesis of vignafuran was tetrabutylammonium fluoride-catalyzed benzo[b]furan ring formation. Ester and coumestrol were synthesize using caarbonylative ring closure methodology catalyzed by a Pd complex.

引用

页码：4339 / 4346

共 22 条

[1] Total syntheses of three natural products, vignafuran, 2-(4-hydroxy-2-methoxyphenyl)-6-methoxybenzofuran-3-carboxylic acid methyl ester, and coumestrol from a common starting material
Hiroya, K
Suzuki, N
Yasuhara, A
Egawa, Y
Kasano, A
Sakamoto, T
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (24): : 4339 - 4346
[2] Crystal Structure of 2-(2-Carboxy-4-hydroxy-6-methoxyphenoxy)-3,5-dichloro-6-hydroxy-4-methylbenzoic Acid 1-Methyl Ester
Jongrungruangchok, Suchada
Aree, Thammarat
Sureram, Sanya
Kittakoop, Prasat
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2013, 32 (11) : 1742 - 1748
[3] Crystal Structure of 2-(2-Carboxy-4-hydroxy-6-methoxyphenoxy)-3,5-dichloro-6-hydroxy-4-methylbenzoic Acid 1-Methyl Ester
Suchada Jongrungruangchok
Thammarat Aree
Sanya Sureram
Prasat Kittakoop
结构化学, 2013, 32 (11) : 1742 - 1748
[4] 4-Hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as potent anti-tumor agents
Hayakawa, I
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Sugano, Y
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (02) : 455 - 458
[5] 2-[(2-Hydroxy-benzylidene)-amino]-5,6-dihydro-4H-cyclopenta [b] Thiophene-3-carboxylic Acid Methyl Ester
Asiri, Abdullah Mohamed
MOLBANK, 2007, (03)
[6] A library synthesis of 4-hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as anti-tumor agents
Hayakawa, I
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Furukawa, H
Naruto, S
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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (17) : 4383 - 4387
[7] SYNTHESES AND STEREOCHEMISTRY OF (+-)-4ALPHA-METHYL-10BETA-HYDROXY-TRANS-1,2,3,4,5,6,7,10-OCTAHYDROPHENANTHRENE-4BETA-CARBOXYLIC ACID LACTONE AND 4 EPIMERS OF(+-)-4-METHYL-1,2,3,4,5,6,7,10-OCTAHYDROPHENANTHRENE-4-CARBOXYLIC ACID
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BANERJEE, AK
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Asiri, Abdullah Mohamed
MOLBANK, 2007, (02)
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GHATAK, UR
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INDIAN JOURNAL OF CHEMISTRY, 1967, 5 (09): : 459 - &
[10] FORMATION OF 2-(DIMETHYLAMINO)-3-HYDROXY-6-METHYL-4H-PYRAN-4-ONE FROM CHLOROKOJIC ACID AND DIMETHYLAMINE - PREPARATION OF 2,3,5-TRIOXOHEXANOIC ACID N,N-DIMETHYLAMIDE
DEKKER, WH
RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS, 1972, 91 (11): : 1338 - &

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