One-pot palladium-catalyzed highly chemo-, regio-, and stereoselective synthesis of trans-stilbene derivatives.: A concise and convenient synthesis of resveratrol

被引：70

作者：

Jeffery, T ^{[1
]}

Ferber, B ^{[1
]}

机构：

[1] UCP, CNRS, ESCOM, Lab Synth Organ Select & Chim Organomet, F-95092 Cergy Pontoise, France

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 01期

关键词：

palladium and compounds; Heck reactions; ammonium salts; vinyltrimethylsilane; resveratrol;

D O I：

10.1016/S0040-4039(02)02317-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient, efficient and highly chemo-, regio-, and stereoselective one-flask synthetic method is reported for the construction of unsymmetrical (or symmetrical) trans-stilbene derivatives based on two sequential Heck-type reactions using tetraalkylammonium salt-based catalyst systems and vinyltrimethylsilane as double bond equivalent. Resveratrol has thus been concisely synthesized. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：193 / 197

页数：5

共 41 条

[1] Stilbenoid dimers: Dissection of a paracyclophane chromophore
Bazan, GC
Oldham, WJ
Lachicotte, RJ
Tretiak, S
Chernyak, V
Mukamel, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) : 9188 - 9204
[2] New NLO stilbene derivatives bearing phosphonate ester electron-withdrawing groups
Belfield, KD
Chinna, C
Schafer, KJ
[J]. TETRAHEDRON LETTERS, 1997, 38 (35) : 6131 - 6134
[3] Boron trichloride/tetra-n-butylammonium iodide:: A mild, selective combination reagent for the cleavage of primary alkyl aryl ethers
Brooks, PR
Wirtz, MC
Vetelino, MG
Rescek, DM
Woodworth, GF
Morgan, BP
Coe, JW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) : 9719 - 9721
[4] Novell stilbenes isolated from the root bark of Ekebergia benguelensis
Chávez, D
Chai, HB
Chagwedera, TE
Gao, Q
Farnsworth, NR
Cordell, GA
Pezzuto, JM
Kinghorn, AD
[J]. TETRAHEDRON LETTERS, 2001, 42 (22) : 3685 - 3688
[5] RADICAL SPIROCYCLIZATION - SYNTHESIS OF AN APPROPRIATELY OXYGENATED SPIRO COMPOUND RELATED TO THE ANTITUMOR ANTIBIOTIC FREDERICAMYCIN-A
CLIVE, DLJ
ANGOH, AG
BENNETT, SM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) : 1339 - 1342
[6] A Horner-Wadsworth-Emmons approach to dipolar and non-dipolar poly(phenylenevinylene)dendrimers
Díez-Barra, E
García-Martínez, JC
Rodríguez-López, J
[J]. TETRAHEDRON LETTERS, 1999, 40 (46) : 8181 - 8184
[7] Effect of protonation-deprotonation processes on the electrooptical properties of bipyridine-containing poly(p-phenylene-vinylene) derivatives
Eichen, Y
Nakhmanovich, G
Gorelik, V
Epshtein, O
Poplawski, JM
Ehrenfreund, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (40) : 10463 - 10470
[8] Minireview -: Biological effects of resveratrol
Frémont, L
[J]. LIFE SCIENCES, 2000, 66 (08) : 663 - 673
[9] A new efficient resveratrol synthesis
Guiso, M
Marra, C
Farina, A
[J]. TETRAHEDRON LETTERS, 2002, 43 (04) : 597 - 598
[10] Heck R.F., 1991, Comprehensive Organic Synthesis, V4, P833, DOI DOI 10.1016/B978-0-08-052349-1.00110-4

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