Tandem cationic aza-Cope rearrangement-Mannich cyclization approach to the core structure of FR901483 via a bridgehead iminium ion

被引:49
作者
Brummond, KM [1 ]
Lu, JL [1 ]
机构
[1] W Virginia Univ, Dept Chem, Morgantown, WV 26506 USA
关键词
D O I
10.1021/ol010029n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] An approach to the potent immunosuppressant FR901483 is described, This route utilizes a tandem cationic aza-Cope rearrangement-Mannich cyclization to generate the core structure of this compound. In addition, this is the first demonstration of this tandem reaction passing through a bridgehead iminium ion.
引用
收藏
页码:1347 / 1349
页数:3
相关论文
共 27 条
[1]  
[Anonymous], [No title captured]
[2]  
Braje WM, 1999, ANGEW CHEM INT EDIT, V38, P2540
[3]   Synthesis of spirolactams from tyrosine amides and related substances [J].
Braun, NA ;
Ciufolini, MA ;
Peters, K ;
Peters, EM .
TETRAHEDRON LETTERS, 1998, 39 (26) :4667-4670
[4]  
FUNK RL, 220 ACS NAT M WASH D
[5]   REDUCTION OF ALPHA-TRIALKYLSILOXY NITRILES WITH DIISOBUTYLALUMINIUM HYDRIDE (DIBAH) - A FACILE PREPARATION OF ALPHA-TRIALKYLSILOXY ALDEHYDES AND THEIR DERIVATIVES [J].
HAYASHI, M ;
YOSHIGA, T ;
NAKATANI, K ;
ONO, K ;
OGUNI, N .
TETRAHEDRON, 1994, 50 (09) :2821-2830
[6]  
HOFFMANN RW, 1985, LIEBIGS ANN CHEM, P2246
[7]   AN IMPROVED METHOD FOR REDUCTIVE ALKYLATION OF AMINES USING TITANIUM(IV) ISOPROPOXIDE AND SODIUM CYANOBOROHYDRIDE [J].
MATTSON, RJ ;
PHAM, KM ;
LEUCK, DJ ;
COWEN, KA .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2552-2554
[8]   Total synthesis of FR901483 [J].
Ousmer, M ;
Braun, NA ;
Ciufolini, MA .
ORGANIC LETTERS, 2001, 3 (05) :765-767
[9]   SYNTHESIS APPLICATIONS OF AZA-COPE REARRANGEMENTS .11. CARBON CARBON BOND FORMATION UNDER MILD CONDITIONS VIA TANDEM CATIONIC AZA-COPE REARRANGEMENT MANNICH REACTIONS - A CONVENIENT SYNTHESIS OF POLYSUBSTITUTED PYRROLIDINES [J].
OVERMAN, LE ;
KAKIMOTO, M ;
OKAZAKI, ME ;
MEIER, GP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6622-6629
[10]   CHARGE AS A KEY COMPONENT IN REACTION DESIGN - THE INVENTION OF CATIONIC CYCLIZATION REACTIONS OF IMPORTANCE IN SYNTHESIS [J].
OVERMAN, LE .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (08) :352-359