Total synthesis of maesanin and analogues

被引：38

作者：

Poigny, S ^{[1
]}

Guyot, M ^{[1
]}

Samadi, M ^{[1
]}

机构：

[1] Museum Natl Hist Nat, CNRS, Chim Lab, F-75231 Paris 05, France

来源：

TETRAHEDRON | 1998年 / 54卷 / 49期

关键词：

D O I：

10.1016/S0040-4020(98)00927-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient total synthesis of maesanin and related quinones is reported, through direct alkylation of 1,2,4,5-tetramethoxybenzene with alkylbromides, followed by oxidation with cerie ammonium nitrate (CAN) which provokes formation of the quinone and deprotection of the more hindered methyl ether in one step, to furnish the desired 2-hydroxydmethoxy-1,4-benzoquinones 1a-h. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：14791 / 14802

页数：12

共 20 条

[1] MESCALINE ANALOGS .2. TETRA-METHOXY-BETA-PHENETHYLAMINE AND PENTA-METHOXY-BETA-PHENETHYLAMINE [J].

BENINGTON, F ;

MORIN, RD ;

CLARK, LC .

JOURNAL OF ORGANIC CHEMISTRY, 1955, 20 (01) :102-108

[2]

BUREAU L, 1985, Plantes Medicinales et Phytotherapie, V19, P17

[3] TOTAL SYNTHESIS OF THE HOST DEFENSE STIMULANT MAESANIN [J].

DANHEISER, RL ;

CHA, DD .

TETRAHEDRON LETTERS, 1990, 31 (11) :1527-1530

[4]

FUKUYAMA Y, 1993, CHEM PHARM BULL, V41, P561, DOI 10.1248/cpb.41.561

[5] TOXICANTS FROM MANGROVE PLANTS .5. ISOLATION OF THE PISCICIDE, 2-HYDROXY-5-METHOXY-3-UNDECYL-1,4 BENZOQUINONE (5-O-METHYLEMBELIN) FROM AEGICERAS-CORNICULATUM [J].

GOMEZ, E ;

DELACRUZGIRON, O ;

DELACRUZ, AA ;

JOSHI, BS ;

CHITTAWONG, V ;

MILES, DH .

JOURNAL OF NATURAL PRODUCTS, 1989, 52 (03) :649-651

[6] STRUCTURE OF MAESAQUINONE [J].

KUBO, I ;

CHAUDHURI, SK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (09) :1131-1134

[7] ISOLATION, STRUCTURE AND SYNTHESIS OF MAESANIN, A HOST DEFENSE STIMULANT FROM AN AFRICAN MEDICINAL PLANT MAESA-LANCEOLATA [J].

KUBO, I ;

KIM, M ;

GANJIAN, I ;

KAMIKAWA, T ;

YAMAGIWA, Y .

TETRAHEDRON, 1987, 43 (12) :2653-2660

[8] ISOLATION, STRUCTURE AND SYNTHESIS OF MAESANIN, A HOST DEFENSE STIMULANT FROM AN AFRICAN MEDICINAL PLANT MAESA-LANCEOLATA [J].

KUBO, I ;

KAMIKAWA, T ;

MIURA, I .

TETRAHEDRON LETTERS, 1983, 24 (36) :3825-3828

[9]

Kubo I., 1989, Studies in Natural Products Chemistry, V5, P815

[10]

KUBO I, 1987, BIOL ACTIVE NATURAL, P185

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