A conjugate addition-dipolar cycloaddition approach towards the synthesis of various alkaloids

被引:0
作者
Flick, Andrew C. [1 ]
Padwa, Albert [1 ]
机构
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
基金
美国国家科学基金会;
关键词
Conjugate addition; dipolar cycloaddition; oxime; bis(phenylsulfonyl)diene; cascade synthesis; reductive cyclization; alkaloid; ENANTIOPURE N-ACYLDIHYDROPYRIDONES; ASYMMETRIC TOTAL-SYNTHESIS; FORMAL TOTAL-SYNTHESIS; PINNAIC ACID; ANNULATION APPROACH; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; STEREOCONTROLLED SYNTHESIS; ORGANOMETALLIC REAGENTS; AZASPIROCYCLIC CORE;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The key element for the synthesis of several alkaloid skeletons consists of a conjugate addition-dipolar cycloaddition of 2,3-bis(phenylsulfonyl)-1,3-butadiene with an appropriate oxime. The resulting cycloadducts are cleaved reductively to provide azapolycyclic scaffolds with strategically placed functionality for further manipulation to the target compounds.
引用
收藏
页码:137 / 161
页数:25
相关论文
共 182 条
[1]   FACILE ROUTE TO 1-PHOSPHORYL-1,3-DIENES AND 1-SULFONYL-1,3-DIENES VIA PALLADIUM-CATALYZED ELIMINATION OF ALLYLIC ACETATES [J].
AKERMARK, B ;
NYSTROM, JE ;
REIN, T ;
BACKVALL, JE ;
HELQUIST, P ;
ASLANIAN, R .
TETRAHEDRON LETTERS, 1984, 25 (50) :5719-5722
[2]   Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine [J].
Andrade, RB ;
Martin, SF .
ORGANIC LETTERS, 2005, 7 (25) :5733-5735
[3]  
[Anonymous], 1985, ORGANIC SULFUR CHEM
[4]  
[Anonymous], 1981, ALKALOIDS CHEM PHYSL
[5]   Absolute stereochemistry of halichlorine; A potent inhibitor of VCAM-1 induction [J].
Arimoto, H ;
Hayakawa, I ;
Kuramoto, M ;
Uemura, D .
TETRAHEDRON LETTERS, 1998, 39 (08) :861-862
[6]   Combining two-directional synthesis and tandem reactions. Part 4: A concise approach to the spirocyclic core of halichlorine and the pinnaic acids [J].
Arini, LG ;
Szeto, P ;
Hughes, DL ;
Stockman, RA .
TETRAHEDRON LETTERS, 2004, 45 (45) :8371-8374
[7]   CYCLOADDITION REACTIONS OF OXIMES - POWERFUL NEW CARBON CARBON BOND FORMING METHODOLOGY [J].
ARMSTRONG, P ;
GRIGG, R ;
WARNOCK, WJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (17) :1325-1327
[8]   TANDEM INTRAMOLECULAR MICHAEL ADDITION AND 1,3-DIPOLAR CYCLOADDITION REACTIONS OF OXIMES - VERSATILE NEW CARBON CARBON BOND FORMING METHODOLOGY [J].
ARMSTRONG, P ;
GRIGG, R ;
SURENDRAKUMAR, S ;
WARNOCK, WJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (17) :1327-1328
[9]  
BARNWELL N, 1994, HETEROCYCLES, V37, P175
[10]  
Bentley K.W., 1965, ISOQUINOLINE ALKALOI