Synthesis of C40-Symmetrical Fully Conjugated Carotenoids by Olefin Metathesis

被引:19
作者
Fontan, Noelia [1 ]
Dominguez, Marta [1 ]
Alvarez, Rosana [1 ]
de Lera, Angel R. [1 ]
机构
[1] Univ Vigo, Dept Quim Organ, Fac Quim, Vigo 36310, Spain
关键词
Polyenes; Polyolefins; Terpenoids; Carotenoids; Metathesis; STILLE REACTION; IN-SITU; EFFICIENT; RUTHENIUM; CATALYSTS; HYDROZIRCONATION; PYRRHOXANTHIN; REARRANGEMENT; BUTENOLIDE; COMPLEXES;
D O I
10.1002/ejoc.201100935
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In an effort to push olefin metathesis to the limits of conjugation in reactants and products, the C-40-symmetrical carotenoids beta,beta-carotene (1), lycopene (2), (3R,3'R)-zeaxanthin (3), and rac-isozeaxanthin (4), which are conjugated undecaenes, have been synthesized from C-21-terminal hexaenes by treatment with Grubbs' second-generation Ru catalyst in dichloromethane at 50 degrees C.
引用
收藏
页码:6704 / 6712
页数:9
相关论文
共 64 条
[1]  
AKIYAMA S, 1979, TETRAHEDRON LETT, P2813
[2]  
[Anonymous], 2002, ANGEW CHEM, V114, P1065
[3]  
[Anonymous], 2008, ANGEW CHEM, V120, P7777
[4]  
BRITTON G, 1995, CAROTENOIDS 1B
[5]  
Britton G., 1996, CAROTENOIDS 2
[6]  
Britton G., 1995, CAROTENOIDS 1A
[7]  
Britton George., 2004, Carotenoids
[8]   Total synthesis of naturally configured pyrrhoxanthin, a carotenoid butenolide from plankton [J].
Burghart, Jochen ;
Brueckner, Reinhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (40) :7664-7668
[9]   Efficient syntheses of the keto-carotenoids canthaxanthin, astaxanthin, and astacene [J].
Choi, S ;
Koo, S .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3328-3331
[10]   ONE-STEP CONVERSION OF CARBONYL-COMPOUNDS INTO ACETYLENES [J].
COLVIN, EW ;
HAMILL, BJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (05) :151-152