Design and synthesis of (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid

被引：10

作者：

Das, Bhaskar C. ^{[1
,2
,3
]}

Kabalka, George W. ^{[4
,5
]}

机构：

[1] Albert Einstein Coll Med, Dept Nucl Med, Bronx, NY 10461 USA

[2] Albert Einstein Coll Med, Dept Dev & Mol Biol, Bronx, NY 10461 USA

[3] Albert Einstein Coll Med, Albert Einstein Coll Canc Ctr, Bronx, NY 10461 USA

[4] Univ Tennessee, Dept Chem, Knoxville, TN 37996 USA

[5] Univ Tennessee, Dept Radiol, Knoxville, TN 37996 USA

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 32期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

retinoids; peptidomimetics; 1,4 Diene and Wittig reaction;

D O I：

10.1016/j.tetlet.2008.05.136

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(E)-4-((3-Ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid, 6, was synthesized in 87% starting from beta-cyclocitral. The target compound 6 was synthesized starting from 1 via a Grignard reaction to form alcohol 2. Compound 2 was converted to Wittig salt 3 by treatment with aldehyde 4 in butyllithium and hexane at -78 degrees C to form ester 5. Ester 5 was saponified and, following acidification, acid 6 was isolated as white solid yield 87%. Published by Elsevier Ltd.

引用

页码：4695 / 4696

页数：2

共 21 条

[1] The promise of retinoids to fight against cancer [J].

Altucci, L ;

Gronemeyer, H .

NATURE REVIEWS CANCER, 2001, 1 (03) :181-193

[2] RETINOIDS AND INHIBITION OF ORNITHINE DECARBOXYLASE ACTIVITY [J].

BOUTWELL, RK .

JOURNAL OF THE AMERICAN ACADEMY OF DERMATOLOGY, 1982, 6 (04) :796-800

[3] A decade of molecular biology of retinoic acid receptors [J].

Chambon, P .

FASEB JOURNAL, 1996, 10 (09) :940-954

[4] REVERSAL BY VITAMIN-A ANALOGS (RETINOIDS) OF HYPERPLASIA INDUCED BY N-METHYL-N'-NITRO-N-NITROSOGUANIDINE IN MOUSE PROSTATE ORGAN-CULTURES [J].

CHOPRA, DP ;

WILKOFF, LJ .

JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1977, 58 (04) :923-930

[5]

CHYTIL F, 1984, PHARMACOL REV, V36, P935

[6] TREATMENT OF 1ST RELAPSE IN ACUTE PROMYELOCYTIC LEUKEMIA WITH ALL-TRANS RETINOIC ACID [J].

DEGOS, L ;

CHOMIENNE, C ;

DANIEL, MT ;

BERGER, R ;

DOMBRET, H ;

FENAUX, P ;

CASTAIGNE, S .

LANCET, 1990, 336 (8728) :1440-1441

[7] Synthesis, of CDE and BCDE molecular fragments of the limonoids havanensin and azadiradione [J].

Fernández-Mateos, A ;

Burón, LM ;

de la Nava, EMM ;

González, RR .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09) :3585-3592

[8] Classical and novel retinoids: their targets in cancer therapy [J].

Fontana, JA ;

Rishi, AK .

LEUKEMIA, 2002, 16 (04) :463-472

[9]

Hong W. K., 1994, RETINOIDS BIOL CHEM, P923

[10]

Kuijpers ALA, 1998, BRIT J DERMATOL, V139, P380

← 1 2 3 →