A new route to highly functionalized heterocyclic rings

被引:23
作者
Parsons, Philip J. [1 ]
Waters, Alexander J.
Walter, Daryl S.
Board, Johnathan
机构
[1] Univ Sussex, Dept Chem, Sch Life Sci, Brighton BN1 9QJ, E Sussex, England
[2] GlaxoSmithKline Res & Dev Ltd, Harlow CM19 5AW, Essex, England
关键词
D O I
10.1021/jo062305n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] A novel cascade reaction has been developed for the rapid construction of heterocyclic rings. The cyclization is thermally induced and does not involve the use of metal ions. This highly efficient construction of furans has been developed during studies directed toward the synthesis of the antibiotic lactonamycin 1.
引用
收藏
页码:1395 / 1398
页数:4
相关论文
共 43 条
[1]   Chelation-controlled Bergman cyclization: Synthesis and reactivity of enediynyl ligands [J].
Basak, A ;
Mandal, S ;
Bag, SS .
CHEMICAL REVIEWS, 2003, 103 (10) :4077-4094
[2]   Silicon-initiated carbonylative carbotricyclization and [2+2+2+1] cycloaddition of enediynes catalyzed by rhodium complexes [J].
Bennacer, B ;
Fujiwara, M ;
Lee, SY ;
Ojima, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17756-17767
[3]   Novel [2+2+2+1] cycloaddition of enediynes catalyzed by rhodium complexes [J].
Bennacer, B ;
Fujiwara, M ;
Ojima, I .
ORGANIC LETTERS, 2004, 6 (20) :3589-3591
[4]   [2+2+2]CYCLOADDITIONS OF ALKYNES TO FURANS AND THIOPHENES - A COBALT-MEDIATED ENOL ETHER WALK [J].
BOESE, R ;
HARVEY, DF ;
MALASKA, MJ ;
VOLLHARDT, KPC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11153-11154
[5]  
BOESE R, 1994, SYNTHESIS-STUTTGART, P1374
[6]   Iron-catalyzed [2π+2π] cycloaddition of α,ω-dienes:: The importance of redox-active supporting ligands [J].
Bouwkamp, Marco W. ;
Bowman, Amanda C. ;
Lobkovsky, Emil ;
Chirik, Paul J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (41) :13340-13341
[7]  
CIGANEK E, 1984, ORG REACTIONS, P1
[8]   STEREOSPECIFIC TOTAL SYNTHESIS OF GIBBERELLIC-ACID - KEY TRICYCLIC INTERMEDIATE [J].
COREY, EJ ;
DANHEISER, RL ;
CHANDRASEKARAN, S ;
SIRET, P ;
KECK, GE ;
GRAS, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (25) :8031-8034
[9]  
COREY EJ, 1978, J AM CHEM SOC, V100, P8034, DOI 10.1021/ja00493a056
[10]   The formal total synthesis of (±)-strychnine via a cobalt-mediated [2+2+2]cycloaddition [J].
Eichberg, MJ ;
Dorta, RL ;
Lamottke, K ;
Vollhardt, KPC .
ORGANIC LETTERS, 2000, 2 (16) :2479-2481