Use of cyclobutyl derivatives as intermediates in the synthesis of 1,2a,3,8b-tetrahydro-2H-cyclobuta[c]chromenes

被引:18
作者
Bernard, AM [1 ]
Floris, C [1 ]
Frongia, A [1 ]
Piras, PP [1 ]
Secci, F [1 ]
机构
[1] Univ Cagliari, Dipartimento Sci Chim, I-09042 Monserrato, Cagliari, Italy
关键词
cyclopropanes; cyclobutanones; electrophilic aromatic substitutions; ring opening; kinetic resolution; capsorubin;
D O I
10.1016/j.tet.2003.11.018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Starting from cyclobutanones and tertiary cyclobutanols several new chromenes containing a cyclobutane ring have been prepared by acid catalyzed intramolecular alkylation of an oxygen-carrying aromatic ring. Interestingly one of the cyclobutanols leads to 3-[(4-methoxyphenoxy)methyl]-2,2,3-trimethylcyclopentanone that is a precursor in the synthesis of the carotenoid pigment capsorubin. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:449 / 457
页数:9
相关论文
共 27 条
[1]   CYCLOBUTANONES AND CYCLOBUTENONES IN NATURE AND IN SYNTHESIS [J].
BELLUS, D ;
ERNST, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (06) :797-827
[2]   Palladium (0) catalyzed nucleophilic substitution on 2-cyclopropylidene-phenoxy ethanes. [J].
Bernard, AM ;
Piras, PP .
SYNTHETIC COMMUNICATIONS, 1997, 27 (05) :709-723
[3]  
Bernard AM, 2002, SYNLETT, P796
[4]  
Bernard AM, 1998, SYNLETT, P668
[5]  
Bernard AM, 1997, SYNLETT, P585
[6]   Synthesis of tertiary cyclobutanols through stereoselective ring expansion of oxaspiropentanes induced by Grignard reagents [J].
Bernard, AM ;
Floris, C ;
Frongia, A ;
Piras, PP .
TETRAHEDRON, 2000, 56 (26) :4555-4563
[7]   CAROTENOIDS AND RELATED-COMPOUNDS .37. STEREOCHEMISTRY AND SYNTHESIS OF CAPSORUBIN [J].
BOWDEN, RD ;
COOPER, RDG ;
HARRIS, CJ ;
MOSS, GP ;
WEEDON, BCL ;
JACKMAN, LM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (07) :1465-1474
[8]   HIGH REGIOSELECTIVE AND STEREOSELECTIVE CYCLO-ADDITION OF A NITRONE TO ALKYLIDENECYCLOPROPANES [J].
BRANDI, A ;
CARLI, S ;
GOTI, A .
HETEROCYCLES, 1988, 27 (01) :17-20
[9]   Optically active cyclobutanones and gamma-butyrolactones from asymmetric alkylidenecyclopropanes [J].
Chevtchouk, T ;
Ollivier, J ;
Salaun, J .
TETRAHEDRON-ASYMMETRY, 1997, 8 (07) :1011-1014
[10]   Enantioselective synthesis of 2-substituted cyclobutanones [J].
Cho, SY ;
Cha, JK .
ORGANIC LETTERS, 2000, 2 (09) :1337-1339