Facile synthesis of lactones and dihydronaphthalenes from methyl 2-isobutenyl (or 2-isopentenyl)cinnamates as the common intermediates

被引：36

作者：

GowriSankar, S

Lee, CG

Kim, JN ^{[1
]}

机构：

[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea

[2] Chonnam Natl Univ, Inst Basic Sci, Kwangju 500757, South Korea

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 37期

基金：

新加坡国家研究基金会;

关键词：

methyl; 2-isobutenylcinnamates; lactones; dihydronaphthalenes; Baylis-Hillman adducts;

D O I：

10.1016/j.tetlet.2004.07.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We prepared three different types of compounds, two alpha(-alkylidene-gamma-butyrolactories and 3,4-dihydronaphthalene-2-carboxylic acid from methyl 2-isobutenylcinnamates or methyl 2-isopentenylcinnamates as the common intermediates, which were derived from the acetates of Baylis-Hillman adducts. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：6949 / 6953

页数：5

相关论文

共 53 条

[1]

ALUTENS M, 2004, J AM CHEM SOC, V126, P1437

[2] Functionalized 1,2-dihydronaphthalenes from the Cu(OTf)2-catalyzed [4+2] cycloaddition of o-alkynyl(oxo)benzenes with alkenes [J].

Asao, N ;

Kasahara, T ;

Yamamoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) :3504-3506

[3] A two steps synthesis of γ-substituted and γ,γ-disubstituted α-(alkylmethylene)-γ-butyrolactones [J].

Ballini, R ;

Marcantoni, E ;

Perella, S .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) :2954-2957

[4] SYNTHESIS OF (+/-)-GADAIN, A NEW LIGNAN FROM JATROPHA-GOSSYPIFOLIA LINN (EUPHORBIACEAE) [J].

BANERJI, J ;

DAS, B .

HETEROCYCLES, 1985, 23 (03) :661-665

[5] Enzyme-assisted asymmetric total synthesis of (-)-podophyllotoxin and (-)-picropodophyllin [J].

Berkowitz, DB ;

Choi, S ;

Maeng, JH .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :847-860

[6] The asymmetric Baylis-Hillman reaction [J].

Brzezinski, LJ ;

Rafel, S ;

Leahy, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) :4317-4318

[7] Ru(II)- and Pt(II)-catalyzed cycloisomerization of ω-aryl-1-alkynes.: Generation of carbocationic species from alkynes and transition metal halides and its interception by an aromatic ring [J].

Chatani, N ;

Inoue, H ;

Ikeda, T ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4913-4918

[8]

Chen MJ, 2000, SYNLETT, P1205

[9] Total synthesis of (+)-blastmycinone, (-)-litsenolide C1, and related natural trisubstituted lactones via alkynyltungsten compounds [J].

Chen, MJ ;

Lo, CY ;

Chin, CC ;

Liu, RS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6362-6367

[10] Indium-promoted preparation of substituted α-methylene-γ-lactones from 2-(bromomethyl)acrylic acid and carbonyl compounds [J].

Choudhury, PK ;

Foubelo, F ;

Yus, M .

TETRAHEDRON LETTERS, 1998, 39 (21) :3581-3584

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