Cross metathesis approach to retinoids and other β-apocarotenoids

被引：8

作者：

Wojtkielewicz, Agnieszka ^{[1
]}

Maj, Jadwiga ^{[1
]}

Dzieszkowska, Agnieszka ^{[1
]}

Morzycki, Jacek Witold ^{[1
]}

机构：

[1] Univ Bialystok, Inst Chem, PL-15443 Bialystok, Poland

来源：

TETRAHEDRON | 2011年 / 67卷 / 36期

关键词：

Cross metathesis; Retinoids; Apocarotenoids; Carotenoids; Polyenes; ACID;

D O I：

10.1016/j.tet.2011.06.086

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cross metathesis (CM) reactions between polyenes, such as beta-carotene, canthaxanthin or retinyl acetate, and various alkenes or dienes in the presence of second generation Hoveyda-Grubbs (H II) or Grubbs (G II) catalysts were investigated. Depending on the cross partner different apocarotenoids were obtained. Cross metathesis reactions of retinyl acetate proved to be fully regioselective. Carotenoid CM reactions afforded mixtures of two products due to competing cleavage of the C11-C12 and C15-C15' double bonds. However, regioselectivity can be controlled by choice of appropriate reaction conditions. The reactions of polyenes with dienes worked better in respect of yields and diastereoselectivities than those with monounsaturated cross partners. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6868 / 6875

页数：8

共 43 条

[1]

Britton G., 1982, CAROTENOID CHEM BIOC, P224

[2]

Cesati RR, 2004, J AM CHEM SOC, V126, P96

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

Chambon, P .

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

[4]

Choi TL, 2001, ANGEW CHEM INT EDIT, V40, P1277, DOI 10.1002/1521-3773(20010401)40:7<1277::AID-ANIE1277>3.3.CO

[5]

2-5

[6] RETINOIC ACID THERAPY FOR PROMYELOCYTIC LEUKEMIA [J].

CHOMIENNE, C ;

BALLERINI, P ;

BALITRAND, N ;

AMAR, M ;

BERNARD, JF ;

BOIVIN, P ;

DANIEL, MT ;

BERGER, R ;

CASTAIGNE, S ;

DEGOS, L .

LANCET, 1989, 2 (8665) :746-747

[7] Recent developments in olefin cross-metathesis [J].

Connon, SJ ;

Blechert, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) :1900-1923

[8] PHASE-IIA STUDY OF FENRETINIDE IN SUPERFICIAL BLADDER-CANCER, USING DNA FLOW-CYTOMETRY AS AN INTERMEDIATE END-POINT [J].

DECENSI, A ;

BRUNO, S ;

COSTANTINI, M ;

TORRISI, R ;

CUROTTO, A ;

GATTESCHI, B ;

NICOLO, G ;

POLIZZI, A ;

PERLOFF, M ;

MALONE, WF ;

BRUZZI, P .

JNCI-JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1994, 86 (02) :138-140

[9] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].

Deiters, A ;

Martin, SF .

CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238

[10]

DEWEGHE PV, 2006, J ORGANOMET CHEM, V691, P5078

← 1 2 3 4 5 →