Synthetic Routes to (+)-cassiol and (-)-cassioside

被引:8
作者
Colombo, MI [1 ]
Ruveda, EA [1 ]
机构
[1] Univ Nacl Rosario, CONICET, Fac Ciencias Bioquim & Farmaceut, Inst Quim Organ Sintesis, RA-2000 Rosario, Santa Fe, Argentina
关键词
enantioselective synthesis; construction of quaternary carbon stereocenters;
D O I
10.1590/S0103-50531998000400002
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review summarizes the sequences recently developed for the total synthesis of the antiulcerogenic compounds (+)-cassiol and its glucoside (-)-cassioside. The discussion is focused on synthetic strategies and on methodologies for the construction of quaternary carbon stereocenters.
引用
收藏
页码:303 / 312
页数:10
相关论文
共 19 条
[1]  
[Anonymous], [No title captured]
[2]   Toward the development of a general chiral auxiliary .5. High diastereofacial selectivity in cycloadditions with trienol silyl ethers: An application to an enantioselective synthesis of (-)-cassioside [J].
Boeckman, RK ;
Liu, YG .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :7984-7985
[3]   DEMONSTRATION OF THE SYNTHETIC POWER OF OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE DIELS-ALDER REACTIONS BY VERY EFFICIENT ROUTES TO CASSIOL AND GIBBERELLIC-ACID [J].
COREY, EJ ;
GUZMANPEREZ, A ;
LOH, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3611-3612
[4]   USEFUL NEW ORGANOMETALLIC REAGENTS FOR SYNTHESIS OF ALLYLIC ALCOHOLS BY NUCLEOPHILIC VINYLATION [J].
COREY, EJ ;
WOLLENBERG, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (15) :2265-2266
[5]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[6]  
2-V
[7]   The origin of the stereoselectivity in the asymmetric Michael reaction using chiral imines secondary enamines under neutral conditions: a computational investigation [J].
Dau, METH ;
Riche, C ;
Dumas, F ;
d'Angelo, J .
TETRAHEDRON-ASYMMETRY, 1998, 9 (06) :1059-1064
[8]   Chiral Lewis acid catalysts in Diels-Alder cycloadditions: Mechanistic aspects and synthetic applications of recent systems [J].
Dias, LC .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 1997, 8 (04) :289-332
[9]   STEREOSPECIFIC SYNTHESIS OF (+)-(3R,4R)-4-METHYL-3-HEPTANOL - ENANTIOMER OF A PHEROMONE OF THE SMALLER EUROPEAN ELM BARK BEETLE (SCOLYTUS-MULTISTRIATUS) [J].
FRATER, G .
HELVETICA CHIMICA ACTA, 1979, 62 (08) :2829-2832
[10]   ASYMMETRIC CREATION OF QUATERNARY CARBON CENTERS [J].
FUJI, K .
CHEMICAL REVIEWS, 1993, 93 (06) :2037-2066