Synthesis of lupiwighteone via a para-Claisen-Cope rearrangement

被引：46

作者：

Al-Maharik, N ^{[1
]}

Botting, NP ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

来源：

TETRAHEDRON | 2003年 / 59卷 / 23期

关键词：

lupiwighteone; Claisen-Cope rearrangement; Mitsunobu reaction;

D O I：

10.1016/S0040-4020(03)00579-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lanthanide catalysed para-Claisen-Cope rearrangement has been used as the key step in a short synthesis of the prenylated isoflavone, lupiwighteone. The Mitsunobu reaction was employed for the 5-O-prenylation of the acid/base sensitive acetylated isoflavone to afford the allyl aryl ether precursor, which was then rearranged under mild conditions in good yield. Rearrangement of the isoflavone gave the 8-prenylisoflavone as a single product, in good yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4177 / 4181

页数：5

共 17 条

[1] ISOFLAVONES FROM PODOCARPUS-AMARUS [J].

CARMAN, RM ;

RUSSELLMAYNARD, JKL ;

SCHUMANN, RC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1985, 38 (03) :485-496

[2] Effects of naturally occurring prenylated flavonoids on enzymes metabolizing arachidonic acid: Cyclooxygenases and lipoxygenases [J].

Chi, YS ;

Jong, HG ;

Son, KH ;

Chang, HW ;

Kang, SS ;

Kim, HP .

BIOCHEMICAL PHARMACOLOGY, 2001, 62 (09) :1185-1191

[3] Measurement of intact sulfate and glucuronide phytoestrogen conjugates in human urine using isotope dilution liquid chromatography-tandem mass spectrometry with [13C3]isoflavone internal standards [J].

Clarke, DB ;

Lloyd, AS ;

Botting, NP ;

Oldfield, MF ;

Needs, PW ;

Wiseman, H .

ANALYTICAL BIOCHEMISTRY, 2002, 309 (01) :158-172

[4] Rearrangement of 5-O-prenyl flavones:: a regioselective access to 6-C-(1,1-dimethylallyl)- and 8-C-(3,3-dimethylallyl)-flavones [J].

Daskiewicz, JB ;

Bayet, C ;

Barron, D .

TETRAHEDRON LETTERS, 2001, 42 (41) :7241-7244

[5] An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement [J].

Gester, S ;

Metz, P ;

Zierau, O ;

Vollmer, G .

TETRAHEDRON, 2001, 57 (06) :1015-1018

[6] ISOFLAVONOIDS OF YELLOW LUPIN .1. NEW COMPLEX ISOFLAVONES IN THE ROOTS OF YELLOW LUPIN (LUPINUS-LUTEUS L, CV BARPINE) [J].

HASHIDOKO, Y ;

TAHARA, S ;

MIZUTANI, J .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1986, 50 (07) :1797-1807

[7] Flavonoid variation in the leaves of Glycyrrhiza glabra [J].

Hayashi, H ;

Yasuma, M ;

Hiraoka, N ;

Ikeshiro, Y ;

Yamamoto, H ;

Yesilada, E ;

Sezik, E ;

Honda, G ;

Tabata, M .

PHYTOCHEMISTRY, 1996, 42 (03) :701-704

[8] CONSTITUTION OF LUTEONE AND PARVISOFLAVONES-A AND PARVISOFLAVONES-B AND SYNTHESIS OF THEIR METHYL ETHERS AND RELATED ISOFLAVONES [J].

JAIN, AC ;

KUMAR, A ;

GUPTA, RC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (01) :279-282

[9] A STUDY OF CLAISEN REARRANGEMENTS OF (1,1-DIMETHYL-3-PROP-2-YNYLOXY)-[4H]-1-BENZOPYRAN-4-ONE DERIVATIVES [J].

JOSHI, SC ;

TRIVEDI, KN .

TETRAHEDRON, 1992, 48 (03) :563-570

[10] HPLC analysis of white lupin isoflavonoids [J].

Katagiri, Y ;

Ibrahim, RK ;

Tahara, S .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2000, 64 (06) :1118-1125

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