The synthesis of a combretastatin A-4 based library and discovery of new cooperative ortho-effects in Wittig reactions leading to (Z)-stilbenes

被引：25

作者：

Harrowven, David C. ^{[1
]}

Guy, Ian L.

Howell, Melanie

Packham, Graham

机构：

[1] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England

[2] Univ Southampton, Sch Med, Canc Res UK Clin Ctr, Southampton SO16 6YD, Hants, England

来源：

SYNLETT | 2006年 / 18期

关键词：

alkenes; antitumor agents; stereoselective synthesis; total synthesis; Wittig reactions;

D O I：

10.1055/s-2006-948200

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of combretastatin A-4 and a small library of analogues led to the discovery of some new cooperative ortho-effects allowing (Z)-stilbenes to be prepared in high yield and diastereorneric ratio.

引用

页码：2977 / 2980

页数：4

共 16 条

[1] Synthesis of water-soluble prodrugs of the cytotoxic agent combretastatin A4.
Bedford, SB
Quarterman, CP
Rathbone, DL
Slack, JA
Griffin, RJ
Stevens, MFG
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (02) : 157 - 160
[2] Microtubule-targeted anticancer agents and apoptosis
Bhalla, KN
[J]. ONCOGENE, 2003, 22 (56) : 9075 - 9086
[3] SYNTHESIS AND EVALUATION OF STILBENE AND DIHYDROSTILBENE DERIVATIVES AS POTENTIAL ANTICANCER AGENTS THAT INHIBIT TUBULIN POLYMERIZATION
CUSHMAN, M
NAGARATHNAM, D
GOPAL, D
CHAKRABORTI, AK
LIN, CM
HAMEL, E
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) : 2579 - 2588
[4] Co-operative ortho-effects on the Wittig reaction.: Interpretation of stereoselectivity in the reaction of ortho-halo-substituted benzaldehydes and benzylidenetriphenylphosphoranes
Dunne, EC
Coyne, EJ
Crowley, PB
Gilheany, DG
[J]. TETRAHEDRON LETTERS, 2002, 43 (13) : 2449 - 2453
[5] Furstner A, 1996, LIEBIGS ANN, P2107
[6] Novel syntheses of cis and trans isomers of combretastatin A-4
Gaukroger, K
Hadfield, JA
Hepworth, LA
Lawrence, NJ
McGown, AT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) : 8135 - 8138
[7] Efficient phenanthrene, helicene, and azahelicene syntheses
Harrowven, DC
Guy, IL
Nanson, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (14) : 2242 - 2245
[8] Study of the Wittig reaction of benzyltriphenylphosphonium salt and benzaldehyde via ylide-mediated phase-transfer catalysis - Substituent and solvent effects
Hwang, JJ
Lin, RL
Shieh, RL
Jwo, JJ
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 142 (02) : 125 - 139
[9] Lawrence NJ, 1999, SYNTHESIS-STUTTGART, P1656
[10] SYNTHESIS OF HALOGENATED TRIMETOQUINOL DERIVATIVES AND EVALUATION OF THEIR BETA-AGONIST AND THROMBOXANE A2 (TXA2) ANTAGONIST ACTIVITIES
MARKOVICH, KM
TANTISHAIYAKUL, V
HAMADA, A
MILLER, DD
ROMSTEDT, KJ
SHAMS, G
SHIN, Y
FRAUNDORFER, PF
DOYLE, K
FELLER, DR
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (03) : 466 - 479

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