An efficient synthesis of (±)-panduratin A and (±)-isopanduratin A, inhibitors of dengue-2 viral activity

被引：36

作者：

Chee, Chin Fei ^{[1
]}

Abdullah, Iskandar ^{[1
]}

Buckle, Michael J. C. ^{[2
]}

Abd Rahman, Noorsaadah ^{[1
]}

机构：

[1] Univ Malaya, Dept Chem, Kuala Lumpur 50603, Malaysia

[2] Univ Malaya, Dept Pharm, Kuala Lumpur 50603, Malaysia

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 03期

关键词：

CONSTITUENTS;

D O I：

10.1016/j.tetlet.2009.11.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Panduratin A and its regioisomer isopanduratin A are synthesized in four steps from (E)-ocimene, [(E)-3,7-dimethyl-1,3,6-octatriene] via a Diels-Alder cycloaddition reaction. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：495 / 498

页数：4

共 12 条

[1]

CHOU TS, 1984, CHEM COMMUN, P1323

[2] Electron transfer-initiated Diels-Alder cycloadditions of 2′-hydroxychalcones [J].

Cong, Huan ;

Ledbetter, Dustin ;

Rowe, Gerard T. ;

Caradonna, John P. ;

Porco, John A., Jr. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9214-+

[3] Aluminosilicate catalysis of chalcone diels-alder reactions [J].

Corbett, Jennifer L. ;

Weavers, Rex T. .

SYNTHETIC COMMUNICATIONS, 2008, 38 (04) :489-498

[4] Activity-guided isolation of constituents of Renealmia nicolaioides with the potential to induce the phase II enzyme quinone reductase [J].

Gu, JQ ;

Park, EJ ;

Vigo, JS ;

Graham, JG ;

Fong, HHS ;

Pezzuto, JM ;

Kinghorn, AD .

JOURNAL OF NATURAL PRODUCTS, 2002, 65 (11) :1616-1620

[5]

Jung EM, 2008, B KOREAN CHEM SOC, V29, P1199

[6] Inhibitory activity of cyclohexenyl chalcone derivatives and flavonoids of fingerroot, Boesenbergia rotunda (L.), towards dengue-2 virus NS3 protease [J].

Kiat, Tan Siew ;

Pippen, Richard ;

Yusof, Rohana ;

Ibrahim, Halijah ;

Norzulaani, Khalid ;

Rahman, Noorsaadah Abd .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (12) :3337-3340

[7] Medicinal foodstuffs.: XXXIV.: Structures of new prenylchalcones and prenylflavanones with TNF-α and aminopeptidase N inhibitory activities from Boesenbergia rotunda [J].

Morikawa, Toshio ;

Funakoshi, Kanako ;

Ninomiya, Kiyofunu ;

Yasuda, Daisuke ;

Miyagawa, Katsutoshi ;

Matsuda, Hisashi ;

Yoshikawa, Masayuki .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2008, 56 (07) :956-962

[8] INSECTICIDAL CONSTITUENTS FROM 4 SPECIES OF THE ZINGIBERACEAE [J].

PANDJI, C ;

GRIMM, C ;

WRAY, V ;

WITTE, L ;

PROKSCH, P .

PHYTOCHEMISTRY, 1993, 34 (02) :415-419

[9] Crinatusins, bioactive Diels-Alder adducts from Cyathocalyx crinatus [J].

Shibata, K ;

Tatsukawa, A ;

Umeoka, K ;

Lee, HS ;

Ochi, M .

TETRAHEDRON, 2000, 56 (45) :8821-8824

[10] (1'RS,2'SR,6'RS)-(2,6-DIHYDROXY-4-METHOXYPHENYL)-[3'-METHYL-2'-(3''-METHYLBUT-2''-ENYL)-6'-PHENYLCYCLOHEX-3'-ENYL]METHANONE (PANDURATIN-A) - A CONSTITUENT OF THE RED RHIZOMES OF A VARIETY OF BOESENBERGIA-PANDURATA [J].

TUNTIWACHWUTTIKUL, P ;

PANCHAROEN, O ;

REUTRAKUL, V ;

BYRNE, LT .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (02) :449-453

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