New synthesis of 3-aryl-2,5-dihydrofurans

被引:8
作者
Chang, Meng-Yang [1 ]
Lin, Chun-Yu
Pai, Chun-Li
机构
[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan
[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan
关键词
D O I
10.3987/COM-06-10795
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We present a straightforward synthesis of 3-aryl-2,5-dihydrofurans by ring contraction of 4-aryl-3,6-dihydro-2H-pyrans with the repeated treatment of MCPBA and BF3-OEt2. The building block 3-aryltetrahydrofuran-3-carboxylic acid with potential biological activities was also prepared.
引用
收藏
页码:1941 / 1948
页数:8
相关论文
共 54 条
[11]   Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid [J].
Bunnage, ME ;
Davies, SG ;
Roberts, PM ;
Smith, AD ;
Withey, JM .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (19) :2763-2776
[12]   RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].
CABRI, W ;
CANDIANI, I .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7
[13]   New synthesis of cis-3,4-diaryl-1-tosylpyrrolidines [J].
Chang, Meng-Yang ;
Pai, Chun-Li ;
Lin, Chun-Yu .
TETRAHEDRON LETTERS, 2006, 47 (22) :3641-3644
[14]   New synthesis of 3-arylpyrrolines [J].
Chang, MY ;
Pai, CL ;
Kung, YH .
TETRAHEDRON LETTERS, 2006, 47 (06) :855-859
[15]   Synthesis of (+/-)-coerulescine and a formal synthesis of (+/-)-horsfiline [J].
Chang, MY ;
Pai, CL ;
Kung, YH .
TETRAHEDRON LETTERS, 2005, 46 (49) :8463-8465
[16]   Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A [J].
Crimmins, MT ;
Zuccarello, JL ;
Cleary, PA ;
Parrish, JD .
ORGANIC LETTERS, 2006, 8 (01) :159-162
[17]   FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB [J].
DE MEIJERE, A ;
MEYER, FE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) :2379-2411
[18]   Synthesis of the N-acetylcysteamine thioester of seco-proansamitocin [J].
Frenzel, T ;
Brünjes, M ;
Quitschalle, M ;
Kirschning, A .
ORGANIC LETTERS, 2006, 8 (01) :135-138
[19]   A general and facile synthesis of substituted furans by palladium-catalyzed cycloisomerization of (Z)-2-En-4-yn-1-ols [J].
Gabriele, B ;
Salerno, G ;
Lauria, E .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :7687-7692
[20]   Synthesis of cyclic and acyclic β-amino acids via chelation-controlled 1,3-dipolar cycloaddition [J].
Hanselmann, R ;
Zhou, JC ;
Ma, P ;
Confalone, PN .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (22) :8739-8741