A novel and practical synthetic route for the total synthesis of lycopene

被引：28

作者：

Shen, Runpu ^{[1
]}

Jiang, Xiaoyue ^{[2
]}

Ye, Weidong ^{[2
]}

Song, Xiaohua ^{[2
]}

Liu, Luo ^{[2
]}

Lao, Xuejun ^{[2
]}

Wu, Chunlei ^{[1
]}

机构：

[1] Shaoxing Univ, Dept Chem & Chem Engn, Shaoxing 312000, Zhejiang, Peoples R China

[2] Zhejiang Med Co Ltd, Xinchang Pharmaceut Factory, Xinchang 312500, Zhejiang, Peoples R China

来源：

TETRAHEDRON | 2011年 / 67卷 / 31期

关键词：

Lycopene; Total synthesis; Wittig-Horner reaction; CAROTENOIDS;

D O I：

10.1016/j.tet.2011.05.104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel route for the total synthesis of lycopene 1 is described. The synthesis is based on: (i) a condensation between 4,4-dimethoxy-3-methylbutanal 4 and methylenebisphosphonic acid tetraethyl ester 5, leading to the C6-phosphonate 6, followed by (ii) a modified Wittig-Horner reaction between 6 and 6-methyl-5-hepten-2-one 7 producing dimethoxy-3,5,9-triene 8, and (iii) another modified Wittig-Horner reaction between C15-phosphonate 2 and C10-triene dialdehyde 3 producing all-E-lycopene. The synthetic steps are easily operated and practical for the large-scale production. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：5610 / 5614

页数：5

共 16 条

[1]

Babler J. H., 2000, Patent, Patent No. [WO0031086, 0031086]

[2] RECENT ADVANCES IN THE SYNTHESIS OF ACHIRAL CAROTENOIDS [J].

BERNHARD, K ;

MAYER, H .

PURE AND APPLIED CHEMISTRY, 1991, 63 (01) :35-44

[3] Expeditious and practical synthesis of lycopene [J].

Choi, Eunho ;

Yeo, Jung Eun ;

Koo, Sangho .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :365-369

[4]

CHRISTOPH W, 1999, Patent No. 0895997

[5]

Edward G., 1995, J NATL CANCER I, V87, P1767

[6]

Gerster H, 1997, J AM COLL NUTR, V16, P109

[7] SYNTHESEN IN DER CAROTINOID-REIHE .6. SYNTHESE VON CROCETINDIALDEHYD UND LYCOPIN [J].

ISLER, O ;

GUTMANN, H ;

LINDLAR, H ;

MONTAVON, M ;

RUEGG, R ;

RYSER, G ;

ZELLER, P .

HELVETICA CHIMICA ACTA, 1956, 39 (02) :463-473

[8]

Joseph L., 1995, NUTR CANC, V24, P257

[9] SYNTHESEN VON CAROTINOIDFARBSTOFFEN .3. TOTALSYNTHESE DES LYCOPINS [J].

KARRER, P ;

EUGSTER, CH ;

TOBLER, E .

HELVETICA CHIMICA ACTA, 1950, 33 (05) :1349-1352

[10]

LIU QH, 2007, Patent No. 101037449

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