A synthetic approach to the communesins

被引:33
作者
George, Jonathan H. [1 ]
Adlington, Robert M. [1 ]
机构
[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England
关键词
alkaloids; indoles; cascade reactions; heterocycles; communesins;
D O I
10.1055/s-2008-1078251
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthetic approach to the communesin family of indole alkaoids has been investigated, with a cascade reaction sequence involving formation of a transient 1-alkoxycarbonylimidazole intermediate and subsequent addition onto an indole as the key step.
引用
收藏
页码:2093 / 2096
页数:4
相关论文
共 20 条
[1]   GENERATION AND REACTIONS OF AZAXYLYLENES [J].
BOWEN, RD ;
DAVIES, DE ;
FISHWICK, CWG ;
GLASBEY, TO ;
NOYCE, SJ ;
STORR, RC .
TETRAHEDRON LETTERS, 1982, 23 (43) :4501-4504
[2]   Diels-Alder reactions of N-sulfonyl substituted aza-ortho-xylylenes generated from the corresponding 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives [J].
Consonni, R ;
Croce, PD ;
Ferraccioli, R ;
LaRosa, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (15) :1809-1814
[3]   Generation of aza-ortho-xylylenes via ring opening of 2-(2-acylaminophenyl)aziridines:: Application in the construction of the communesin ring system [J].
Crawley, Seth L. ;
Funk, Raymond L. .
ORGANIC LETTERS, 2006, 8 (18) :3995-3998
[4]   A synthetic approach to nomofungin/communesin B [J].
Crawley, SL ;
Funk, RL .
ORGANIC LETTERS, 2003, 5 (18) :3169-3171
[5]   Communesins G and H, new alkaloids from the psychrotolerant fungus Penicillium rivulum [J].
Dalsgaard, PW ;
Blunt, JW ;
Munro, MHG ;
Frisvad, JC ;
Christophersen, C .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (02) :258-261
[6]   A SIMPLE ROUTE TO C-FUNCTIONALIZED AZAXYLYLENES AND DIAZAXYLYLENES [J].
FISHWICK, CWG ;
STORR, RC ;
MANLEY, PW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (19) :1304-1305
[7]   Total synthesis of (±)-perophoramidine [J].
Fuchs, JR ;
Funk, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) :5068-5069
[8]   New insecticidal compounds, communesins C, D and E, from Penicillium expansum link MK-57 [J].
Hayashi, H ;
Matsumoto, H ;
Akiyama, K .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2004, 68 (03) :753-756
[9]  
HODGETTS I, 1984, TETRAHEDRON LETT, V25, P545
[10]   New communesin derivatives from the fungus Penicillium sp derived from the Mediterranean sponge Axinella verrucosa [J].
Jadulco, R ;
Edrada, RA ;
Ebel, R ;
Berg, A ;
Schaumann, K ;
Wray, V ;
Steube, K ;
Proksch, P .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (01) :78-81