The synthesis of (S)-(+)-gossypol via an asymmetric Ullmann coupling

被引:54
作者
Meyers, AI
Willemsen, JJ
机构
[1] Department of Chemistry, Colorado State University, Fort Collins
关键词
D O I
10.1039/a703043f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first asymmetric total synthesis of (S)-(+)-gossypol is described using chiral oxazolines as the naphthyl substituent in a highly diastereoselective aryl-aryl coupling.
引用
收藏
页码:1573 / 1574
页数:2
相关论文
共 34 条
[1]   Structure of gossypol XIV Apogossypolic acid [J].
Adams, R ;
Morris, RC ;
Butterbaugh, DJ ;
Kirkpatrick, EC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1938, 60 :2191-2193
[2]   H-1 AND C-13 NMR-STUDIES OF TETRABUTYLAMMONIUM SALTS OF GOSSYPOL IN CHLOROFORM SOLUTION [J].
BRYCKI, B ;
BRZEZINSKI, B ;
MARCINIAK, B ;
PASZYC, S .
SPECTROSCOPY LETTERS, 1991, 24 (04) :509-518
[3]   H-1-NMR STUDIES OF GOSSYPOL AND ITS COMPLEXES WITH SOME ORGANIC-COMPOUNDS [J].
BRZEZINSKI, B ;
OLEJNIK, J ;
PASZYC, S ;
ARIPOV, TF .
JOURNAL OF MOLECULAR STRUCTURE, 1990, 220 :261-268
[4]   ANTIVIRAL ACTIVITY OF GOSSYPOL AND APOGOSSYPOL [J].
DORSETT, PH ;
KERSTINE, EE ;
POWERS, LJ .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1975, 64 (06) :1073-1075
[5]   STUDIES IN THE NAPHTHALENE SERIES .3. SYNTHESIS OF APOGOSSYPOL HEXAMETHYL ETHER [J].
EDWARDS, JD ;
CASHAW, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (09) :2283-2285
[6]  
Fuson R. C., 1955, ORG SYNTH, VIII, P339
[7]   THE CHEMISTRY OF 2-OXAZOLINES (1985-PRESENT) [J].
GANT, TG ;
MEYERS, AI .
TETRAHEDRON, 1994, 50 (08) :2297-2360
[8]  
GORYUNOVA L V, 1969, Farmakologiya i Toksikologiya (Moscow), V32, P615
[9]   ABSOLUTE-CONFIGURATION OF GOSSYPOL [J].
HUANG, L ;
SI, YK ;
SNATZKE, G ;
ZHENG, DK ;
ZHOU, J .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1988, 53 (11A) :2664-2666
[10]   OPTICAL STABILITY OF GOSSYPOL [J].
JAROSZEWSKI, JW ;
STROMHANSEN, T ;
HANSEN, LL .
CHIRALITY, 1992, 4 (04) :216-221