New convenient synthesis of iridol. An approach to the synthesis of ubiquinones

被引:14
作者
Bovicelli, P
Antonioletti, R
Barontini, M
Borioni, G
Bernini, R
Mincione, E
机构
[1] Univ Roma La Sapienza, Dipartimento Chim, Sez Roma, CNR,Ist Chim Biomol, I-00185 Rome, Italy
[2] Univ Tuscia, Dipartimento ABAC, I-01100 Viterbo, Italy
关键词
ubiquinones; coenzyme Q; iridol; halogenations;
D O I
10.1016/j.tetlet.2005.01.001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A strategy for the synthesis of ubiquinones, in which iridol is the key intermediate, has been developed, together with a new convenient synthesis of iridol (2,3-dimethoxy-5-methylphenol) starting from the easily available 4-methylphenol and using mild conditions and friendly and high-yielding reactions. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1255 / 1257
页数:3
相关论文
共 20 条
[1]   THE COPPER CATALYZED REACTION OF SODIUM METHOXIDE WITH ARYL BROMIDES - A MECHANISTIC STUDY LEADING TO A FACILE SYNTHESIS OF ANISOLE DERIVATIVES [J].
AALTEN, HL ;
VANKOTEN, G ;
GROVE, DM ;
KUILMAN, T ;
PIEKSTRA, OG ;
HULSHOF, LA ;
SHELDON, RA .
TETRAHEDRON, 1989, 45 (17) :5565-5578
[2]   METAL IONS AND COMPLEXES IN ORGANIC REACTIONS .8. COPPER-CATALYSED REDUCTION OF ARYL HALIDES BY ALKOXIDES [J].
BACON, RGR ;
RENNISON, SC .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (02) :308-&
[3]   METAL IONS AND COMPLEXES IN ORGANIC REACTIONS .7. COPPER-PROMOTED HYDROGEN TRANSFER FROM AROMATIC DONORS TO HALIDES [J].
BACON, RGR ;
STEWART, OJ .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (02) :301-&
[4]   METAL IONS AND COMPLEXES IN ORGANIC REACTIONS .9. COPPER(1)-CATALYSED CONVERSION OF ARYL HALIDES INTO ALKYL ARYL ETHERS [J].
BACON, RGR ;
RENNISON, SC .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (02) :312-&
[5]   Disulfide bonds are generated by quinone reduction [J].
Bader, MW ;
Xie, T ;
Yu, CA ;
Bardwell, JCA .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (34) :26082-26088
[6]  
BENZENDALE IR, 2001, SYNLETT, V9, P1482
[8]   Selective halogenation of flavanones [J].
Bovicelli, P ;
Bernini, R ;
Antonioletti, R ;
Mincione, E .
TETRAHEDRON LETTERS, 2002, 43 (32) :5563-5567
[9]  
BOVICELLI P, 2001, SYNTHETIC COMMUN, V31, P67
[10]   Quinones as the redox signal for the Arc two-component system of bacteria [J].
Georgellis, D ;
Kwon, O ;
Lin, ECC .
SCIENCE, 2001, 292 (5525) :2314-2316