An improved synthesis of resveratrol

被引:44
作者
Farina, A [1 ]
Ferranti, C [1 ]
Marra, C [1 ]
机构
[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
关键词
resveratrol; Heck reaction; Wittig reaction; stilbene; protective group;
D O I
10.1080/14786410500059532
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this article we report an improved total synthesis of resveratrol, increasing the overall yield from 22 to 71%. The synthesis reported in our previous publication was made up of two fundamental steps: a Wittig reaction and a Heck coupling. Here we studied these steps separately to increase the individual yields. The yield of the Wittig reaction was increased up to 98%; however, we could not find better reaction conditions for the Heck coupling than those reported in the previous article.
引用
收藏
页码:247 / 252
页数:6
相关论文
共 20 条
[1]   Antioxidant activity and protective effect on DNA cleavage of resveratrol [J].
Acquaviva, R ;
Russo, A ;
Campisi, A ;
Sorrenti, V ;
Di Giacomo, C ;
Barcellona, ML ;
Avitabile, M ;
Vanella, A .
JOURNAL OF FOOD SCIENCE, 2002, 67 (01) :137-141
[2]   3,5-bis(trifluoromethyl)phenyl sulfones in the modified Julia olefination:: application to the synthesis of resveratrol [J].
Alonso, DA ;
Nájera, C ;
Varea, M .
TETRAHEDRON LETTERS, 2004, 45 (03) :573-577
[3]   Simple synthesis of 5-substituted resorcinols: A revisited family of interesting bioactive molecules [J].
Alonso, E ;
Ramon, DJ ;
Yus, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :417-421
[4]   A short and efficient synthetic approach to hydroxy (E)-stilbenoids via solid-phase cross metathesis [J].
Chang, S ;
Na, Y ;
Shin, HJ ;
Choi, E ;
Jeong, LS .
TETRAHEDRON LETTERS, 2002, 43 (41) :7445-7448
[5]   AN ANTIPLATELET PRINCIPLE OF VERATRUM-FORMOSANUM [J].
CHUNG, MI ;
TENG, CM ;
CHENG, KL ;
KO, FN ;
LIN, CN .
PLANTA MEDICA, 1992, 58 (03) :274-276
[6]   Antioxidant activity of resveratrol and alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated fatty acids [J].
Frémont, L ;
Belguendouz, L ;
Delpal, S .
LIFE SCIENCES, 1999, 64 (26) :2511-2521
[7]   WITTIG REACTION USING METHYLSULFINYL CARBANION-DIMETHYL SULFOXIDE [J].
GREENWALD, R ;
COREY, EJ ;
CHAYKOVSKY, M .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (04) :1128-&
[8]   A new efficient resveratrol synthesis [J].
Guiso, M ;
Marra, C ;
Farina, A .
TETRAHEDRON LETTERS, 2002, 43 (04) :597-598
[9]   Cardioprotective effect of resveratrol, a natural antioxidant derived from grapes [J].
Hung, LM ;
Chen, JK ;
Huang, SS ;
Lee, RS ;
Su, MJ .
CARDIOVASCULAR RESEARCH, 2000, 47 (03) :549-555
[10]   One-pot palladium-catalyzed highly chemo-, regio-, and stereoselective synthesis of trans-stilbene derivatives.: A concise and convenient synthesis of resveratrol [J].
Jeffery, T ;
Ferber, B .
TETRAHEDRON LETTERS, 2003, 44 (01) :193-197