Generation of aza-ortho-xylylenes via ring opening of 2-(2-acylaminophenyl)aziridines:: Application in the construction of the communesin ring system

被引:80
作者
Crawley, Seth L. [1 ]
Funk, Raymond L. [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词
D O I
10.1021/ol061461d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new protocol for generating aza-ortho-xylylenes via acid-catalyzed or fluoride-promoted ring opening of 2-(2-acylaminophenyl) aziridines is described. This methodology has been exploited in the rapid construction of a hexacyclic substructure of communesin B.
引用
收藏
页码:3995 / 3998
页数:4
相关论文
共 38 条
[1]   ZrCl4 as a new and efficient catalyst for the opening of epoxide rings by amines [J].
Chakraborti, AK ;
Kondaskar, A .
TETRAHEDRON LETTERS, 2003, 44 (45) :8315-8319
[2]   Rapid route to 3,4-substituted Indoles via a directed ortho metalation - Retro-Mannich sequence [J].
Chauder, B ;
Larkin, A ;
Snieckus, V .
ORGANIC LETTERS, 2002, 4 (05) :815-817
[3]   LANTHANIDE(III) TRIFLUOROMETHANESULFONATES AS EXTRAORDINARILY EFFECTIVE NEW CATALYSTS FOR THE AMINOLYSIS OF 1,2-EPOXIDES [J].
CHINI, M ;
CROTTI, P ;
FAVERO, L ;
MACCHIA, F ;
PINESCHI, M .
TETRAHEDRON LETTERS, 1994, 35 (03) :433-436
[4]  
COMMUNESINS A, 1993, TETRAHEDRON LETT, V34, P2355
[5]  
COMMUNESINS A, 2001, J ORG CHEM, V66, P8717
[6]  
COMMUNESINS BCD, 2004, J NAT PRODUCTS, V67, P78
[7]  
COMMUNESINS G, 2005, J NAT PRODUCTS, V68, P258
[8]   Expeditious synthesis of aziridine-based cofactor mimics [J].
Comstock, LR ;
Rajski, SR .
TETRAHEDRON, 2002, 58 (30) :6019-6026
[9]   A synthetic approach to nomofungin/communesin B [J].
Crawley, SL ;
Funk, RL .
ORGANIC LETTERS, 2003, 5 (18) :3169-3171
[10]   On the effect of ring substituents in the carbonylation of aziridines [J].
Davoli, P ;
Forni, A ;
Moretti, I ;
Prati, F ;
Torre, G .
TETRAHEDRON, 2001, 57 (09) :1801-1812