Expeditious and practical synthesis of lycopene

被引:10
作者
Choi, Eunho [1 ]
Yeo, Jung Eun [2 ]
Koo, Sangho [1 ,2 ]
机构
[1] Myong Ji Univ, Dept Nano Sci & Engn, Yongin 449728, South Korea
[2] Myong Ji Univ, Dept Chem, Yongin 449728, South Korea
关键词
allylic oxidation; carotenoids; elimination; lycopene synthesis; olefination; sulfone chemistry;
D O I
10.1002/adsc.200700484
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Our lycopene synthesis highlights the expeditious assembly of the carbon skeleton by the use of a readily available ten-carbon unit, geraniol, rather than the original natural five-carbon building block, isopentenyl pyrophosphate. Furthermore, four oxidation steps by the enzyme desaturases to produce the conjugated carbon-carbon double bonds of lycopene are merged into one-pot double elimination reactions in our synthesis. These accomplished the highly efficient synthesis of all-(E)-lycopene from geraniol through a seven-step sequence in 51% overall yield.
引用
收藏
页码:365 / 369
页数:5
相关论文
共 16 条
[1]  
Cane D.E., 1999, COMPREHENSIVE NATURA, V2
[2]   Recent advances in industrial carotenoid synthesis [J].
Ernst, H .
PURE AND APPLIED CHEMISTRY, 2002, 74 (08) :1369-1382
[3]   Sulfone coupling and double-elimination strategy for carotenoid synthesis [J].
Guha, SK ;
Koo, S .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9662-9665
[4]   SYNTHESIS, ISOLATION, AND NMR-SPECTROSCOPIC CHARACTERIZATION OF 14 (Z)-ISOMERS OF LYCOPENE AND OF SOME ACETYLENIC DIDEHYDROLYCOPENES AND TETRADEHYDROLYCOPENES [J].
HENGARTNER, U ;
BERNHARD, K ;
MEYER, K ;
ENGLERT, G ;
GLINZ, E .
HELVETICA CHIMICA ACTA, 1992, 75 (06) :1848-1865
[5]   ANHYDROUS TERT-BUTYL HYDROPEROXIDE IN TOLUENE - THE PREFERRED REAGENT FOR APPLICATIONS REQUIRING DRY TBHP [J].
HILL, JG ;
ROSSITER, BE ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20) :3607-3608
[6]   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
[7]   Allylic sulfones containing triene moieties as key synthons for carotenoid synthesis [J].
Ji, M ;
Choi, H ;
Jeong, YC ;
Jin, JQ ;
Baik, W ;
Lee, S ;
Kim, JS ;
Park, M ;
Koo, S .
HELVETICA CHIMICA ACTA, 2003, 86 (07) :2620-2628
[8]  
Ji MK, 2001, ANGEW CHEM INT EDIT, V40, P3627, DOI 10.1002/1521-3773(20011001)40:19<3627::AID-ANIE3627>3.0.CO
[9]  
2-E
[10]   SYNTHESEN VON CAROTINOIDFARBSTOFFEN .3. TOTALSYNTHESE DES LYCOPINS [J].
KARRER, P ;
EUGSTER, CH ;
TOBLER, E .
HELVETICA CHIMICA ACTA, 1950, 33 (05) :1349-1352