Bargellini condensation of coumarins.: Expeditious route to o-carboxyvinylphenoxyisobutyric acids and application to the synthesis of sesquiterpenes helianane, heliannuol A and heliannuol C

被引：31

作者：

Biswas, Bidyut ^{[1
]}

Sen, Prabir K. ^{[2
]}

Venkateswaran, Ramanathapuram V. ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, W Bengal, India

[2] Haldia Govt Coll, Dept Chem, Midnapore, W Bengal, India

来源：

TETRAHEDRON | 2007年 / 63卷 / 48期

关键词：

bargellini condensation; o-carboxyvinylphenoxyisobutyric acids; heliannuols; helianane; ring-closing metathesis;

D O I：

10.1016/j.tet.2007.09.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct Bargellini condensation of coumarins involving reaction with chloroform and acetone in the presence of aqueous sodium hydroxide furnished o-carboxyvinylphenoxyisobutyric acids in good yields. The utility of this new useful protocol was demonstrated by the transformation of the three diesters 9b, 9f and 9g to the sesquiterpenes helianane 4, heliannuol A 2 and heliannuol C 3, respectively. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：12026 / 12036

页数：11

共 20 条

[1]

Bargellini G., 1906, GAZZ CHIM ITAL, V36, P329

[2] The synthesis of heliannuol C, an allelochemical from Helianthus annuus [J].

Biswas, Bidyut ;

Sen, Prabir K. ;

Venkateswaran, Ramanathapuram V. .

TETRAHEDRON LETTERS, 2006, 47 (24) :4019-4021

[3] A NEW METHOD FOR DIRECTED CONVERSION OF PHENOXY GROUPING INTO A VARIETY OF CYCLIC POLYFUNCTIONAL SYSTEMS [J].

COREY, EJ ;

BARCZA, S ;

KLOTMANN, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (17) :4782-&

[4] An efficient synthesis of a dual PPAR α/γ agonist and the formation of a sterically congested α-aryloxyisobutyric acid via a Bargellini reaction [J].

Cvetovich, RJ ;

Chung, JYL ;

Kress, MH ;

Amato, JS ;

Matty, L ;

Weingarten, MD ;

Tsay, FR ;

Li, Z ;

Zhou, G .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8560-8563

[5] Synthesis of heliannuols A and K, allelochemicals from cultivar sunflowers and the marine metabolite helianane, unusual sesquiterpenes containing a benzoxocane ring system [J].

Ghosh, Subrata ;

Tuhina, Kazi ;

Bhowmik, Dipal R. ;

Venkateswaran, Ramanathapuram V. .

TETRAHEDRON, 2007, 63 (03) :644-651

[6] SOME SUBSTITUTED ALPHA-(ARYLOXY)-ISOBUTYRIC ACIDS AND AMIDES [J].

GILMAN, H ;

WILDER, GR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (24) :6644-6646

[7] TOTAL SYNTHESIS OF (+/-)-HELIANNUOL-A [J].

GRIMM, EL ;

LEVAC, S ;

TRIMBLE, LA .

TETRAHEDRON LETTERS, 1994, 35 (37) :6847-6850

[8]

HARISSON B, 1997, J ORG CHEM, V62, P2646

[9] A catalytic asymmetric synthesis of chiral glycidic acid derivatives through chiral dioxirane-mediated catalytic asymmetric epoxidation of cinnamic acid derivatives [J].

Imashiro, R ;

Seki, M .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (12) :4216-4226

[10] Enantioselective total synthesis of (-)-heliannuol A [J].

Kishuku, H ;

Shindo, M ;

Shishido, K .

CHEMICAL COMMUNICATIONS, 2003, (03) :350-351

← 1 2 →