Suzuki cross-coupling reactions of γ-alkylidenebutenolides:: Application to the synthesis of vulpinic acid

被引：35

作者：

Ahmed, Z ^{[1
]}

Langer, P ^{[1
]}

机构：

[1] Ernst Moritz Arndt Univ Greifswald, Inst Chem & Biochem, D-17487 Greifswald, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 11期

关键词：

D O I：

10.1021/jo049780a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Hydroxy-gamma-alkylidenebutenolides were efficiently functionalized by Suzuki cross-coupling reactions via the corresponding enol triflates. The natural product vulpinic acid was prepared by this methodology.

引用

页码：3753 / 3757

页数：5

共 34 条

[1] STUDIES ON CHEMISTRY OF LICHENS .14. STRUCTURE OF CALYCIN [J].

AKERMARK, B .

ACTA CHEMICA SCANDINAVICA, 1961, 15 (08) :1695-&

[2] The β-elimination route to stereodefined γ-alkylidenebutenolides [J].

Brückner, R .

CHEMICAL COMMUNICATIONS, 2001, (02) :141-152

[3] CHEMISTRY OF ENOL SILYL ETHERS .5. A NOVEL CYCLOAROMATIZATION REACTION - REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED METHYL SALICYLATES [J].

CHAN, TH ;

BROWNBRIDGE, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (10) :3534-3538

[4] Norbadione A: Synthetic approach to the bis(pulvinic acid) moiety and cesium-complexation studies [J].

Desage-El Murr, M ;

Nowaczyk, S ;

Le Gall, T ;

Mioskowski, C ;

Amekraz, B ;

Moulin, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (11) :1289-1293

[5] Chemical and biological investigation of the fungus Pulveroboletus ravenelii [J].

Duncan, CJG ;

Cuendet, M ;

Fronczek, FR ;

Pezzuto, JM ;

Mehta, RG ;

Hamann, MT ;

Ross, SA .

JOURNAL OF NATURAL PRODUCTS, 2003, 66 (01) :103-107

[6] TOXICITY AND ANTIFEEDANT ACTIVITY OF LICHEN COMPOUNDS AGAINST THE POLYPHAGOUS HERBIVOROUS INSECT SPODOPTERA-LITTORALIS [J].

EMMERICH, R ;

GIEZ, I ;

LANGE, OL ;

PROKSCH, P .

PHYTOCHEMISTRY, 1993, 33 (06) :1389-1394

[7]

Gill M, 1987, Fortschr Chem Org Naturst, V51, P1

[8]

Gorth FC, 1998, EUR J ORG CHEM, V1998, P1055

[9]

Knight D.W., 1994, CONTEMP ORG SYNTH, V1, P287, DOI DOI 10.1021/CR60230A002

[10] SYNTHESIS OF PULVINIC ACID PIGMENTS OF LICHEN AND FUNGI [J].

KNIGHT, DW ;

PATTENDEN, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (16) :660-661

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