Synthesis of deoxyvariolin B

被引:50
作者
Alvarez, M [1 ]
Fernández, D
Joule, JA
机构
[1] Univ Barcelona, Fac Farm, Lab Quim Organ, E-08028 Barcelona, Spain
[2] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
关键词
D O I
10.1016/S0040-4039(00)01916-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of deoxyvariolin B (5) is described. The tricyclic pyridopyrrolopyrimidone (11) was prepared from 7-azaindole via lithiation at C-2, introduction of an aminoethyl side-chain, then closure of the third ring. A heteroaryl palladium(0)-catalysed coupling reaction was used to introduce a pyrimidine substituent at C-5. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:315 / 317
页数:3
相关论文
共 14 条
[1]   Synthesis of 1,2-dihydropyrrolo[1,2-c]pyrimidin-1-ones [J].
Alvarez, M ;
Fernández, D ;
Joule, JA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (03) :249-255
[2]  
ALVAREZ M, 2000, SYNTHESIS-STUTTGART, P615
[3]   HETEROCYCLIZATIONS .8. NEW POLYCYCLIC PYRIMIDINES WITH BRIDGE-HEAD NITROGEN [J].
CAPUANO, L ;
SCHREPFER, HJ ;
MULLER, K ;
ROOS, H .
CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (03) :929-936
[4]  
Charya SB, 1998, J INDIAN CHEM SOC, V75, P46
[5]   Synthesis of 2-substituted-1H-pyrrolo[2,3-b]pyridines: Preparation of 7-azaolivacine analogue and 7-azaindolopyridopyrimidine derivatives. [J].
Desarbre, E ;
Coudret, S ;
Meheust, C ;
Merour, JY .
TETRAHEDRON, 1997, 53 (10) :3637-3648
[6]   Synthetic studies towards the 2-aminopyrimidine alkaloids variolins and meridianins from marine origin [J].
Fresneda, PM ;
Molina, P ;
Delgado, S ;
Bleda, JA .
TETRAHEDRON LETTERS, 2000, 41 (24) :4777-4780
[8]   A NEW INDOLE SYNTHESIS [J].
LORENZ, RR ;
TULLAR, BF ;
KOELSCH, CF ;
ARCHER, S .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (08) :2531-&
[9]   STANNYLATION REACTIONS AND CROSS-COUPLINGS IN PYRIMIDINES [J].
MAJEED, AJ ;
ANTONSEN, O ;
BENNECHE, T ;
UNDHEIM, K .
TETRAHEDRON, 1989, 45 (04) :993-1006
[10]   New procedures for the synthesis of heterocyclic substituted and 2,4-difunctionalized pyrimidines [J].
Martinez, AG ;
Fernandez, AH ;
Jimenez, FM ;
Martinez, PJM ;
Martin, CA ;
Subramanian, LR .
TETRAHEDRON, 1996, 52 (23) :7973-7982