Transition metals in organic synthesis, part 85.: A general approach to 1,6-dioxygenated carbazole alkaloids -: First total synthesis of clausine G, clausine I, and clausine Z

被引:37
作者
Boerger, Carsten [1 ]
Knoelker, Hans-Joachim [1 ]
机构
[1] Tech Univ Dresden, Dept Chem, D-01069 Dresden, Germany
关键词
alkaloids; antibiotics; catalysis; cyclizations; palladium;
D O I
10.1055/s-2008-1077855
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Using the palladium-catalyzed construction of the carbazole framework, a highly efficient route to 1,6-dioxygenated carbazole alkaloids has been developed and applied to the total synthesis of clausenine, 6-methoxymurrayanine, clausenol, clausine G, clausine I, and clausine Z. The three latter natural products have been synthesized for the first time.
引用
收藏
页码:1698 / 1702
页数:5
相关论文
共 53 条
[1]   Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes [J].
Ackermann, Lutz ;
Althammer, Andreas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1627-1629
[2]  
AKERMARK B, 1975, J ORG CHEM, V40, P1365, DOI 10.1021/jo00897a048
[3]   N-H carbazole synthesis from 2-chloroanilines via consecutive amination and C-H activation [J].
Bedford, Robin B. ;
Betham, Michael .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9403-9410
[4]   SYNTHESIS OF CARBAZOLE ALKALOIDS [J].
BERGMAN, J ;
PELCMAN, B .
PURE AND APPLIED CHEMISTRY, 1990, 62 (10) :1967-1976
[5]   exo-2-oxazolidinone dienes in the total synthesis of the natural carbazoles, 6-methoxymurrayanine and clausenine [J].
Bernal, Pablo ;
Benavides, Adriana ;
Bautista, Rafael ;
Tamariz, Joaquin .
SYNTHESIS-STUTTGART, 2007, (13) :1943-1948
[6]   CLAUSENOL AND CLAUSENINE - 2 CARBAZOLE ALKALOIDS FROM CLAUSENA-ANISATA [J].
CHAKRABORTY, A ;
CHOWDHURY, BK ;
BHATTACHARYYA, P .
PHYTOCHEMISTRY, 1995, 40 (01) :295-298
[7]  
Chakraborty D P, 1991, Fortschr Chem Org Naturst, V57, P71
[8]  
Chakraborty D.P., 1993, The Alkaloids, V44, P257
[9]   Synthesis of indoles: Efficient functionalisation of the 7-position [J].
Charrier, Nicolas ;
Demont, Emmanuel ;
Dunsdon, Rachel ;
Maile, Graham ;
Naylor, Alan ;
O'Brien, Alistair ;
Redshaw, Sally ;
Theobald, Pam ;
Vesey, David ;
Walter, Daryl .
SYNTHESIS-STUTTGART, 2006, (20) :3467-3477
[10]  
Choi T. A., 2006, MED CHEM RES, V15, P28