An expedient synthesis of 3-acyltetramic acids of the melophlin family from α-aminoesters and immobilized Ph3PCCO

被引:40
作者
Schobert, R [1 ]
Jagusch, C [1 ]
机构
[1] Univ Bayreuth, Organ Chem Lab, D-95440 Bayreuth, Germany
关键词
tetramic acids; phosphorus ylides; solid phase organic synthesis; immobilized reagents; melophlins; microwave;
D O I
10.1016/j.tet.2005.01.036
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The naturally occurring 3-acyltetramic acids (3-acylpyrrolidine-2,4-diones) melophlin A, B, C and G were prepared in few steps from alpha-aminoesters or their hydrochlorides by cyclization with Ph3PCCO under mild conditions. The employment of immobilized, polystyrene-bound ylide greatly simplifies the removal of by-product Ph3PO and of other impurities. Various 3-acylation methods were assessed. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2301 / 2307
页数:7
相关论文
共 40 条
[1]   Regioselective Dieckmann cyclisations leading to enantiopure highly functionalised tetramic acid derivatives [J].
Andrews, MD ;
Brewster, AG ;
Crapnell, KM ;
Ibbett, AJ ;
Jones, T ;
Moloney, MG ;
Prout, K ;
Watkin, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (02) :223-235
[2]   Melophlins A and B, novel tetramic acids reversing the phenotype of ras-transformed cells, from the marine sponge Melophlus sarassinorum [J].
Aoki, S ;
Higuchi, K ;
Ye, Y ;
Satari, R ;
Kobayashi, M .
TETRAHEDRON, 2000, 56 (13) :1833-1836
[3]   AN ENANTIOSELECTIVE AND HIGHLY CONVERGENT SYNTHESIS OF (+)-IKARUGAMYCIN [J].
BOECKMAN, RK ;
WEIDNER, CH ;
PERNI, RB ;
NAPIER, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :8036-8037
[4]   Cyclisation of novel amino oxo esters to tetramic acids - Density functional theory study of the reaction mechanism [J].
Detsi, A ;
Afantitis, A ;
Athanasellis, G ;
Markopoulos, J ;
Igglessi-Markopoulou, O ;
Skylaris, CK .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (23) :4593-4600
[5]   Total synthesis of the polyenoyltetramic acid mycotoxin erythroskyrine [J].
Dixon, DJ ;
Ley, SV ;
Gracza, T ;
Szolcsanyi, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08) :839-841
[6]   Total synthesis of the plasmoidal pigment physarorubinic acid, a polyenoyl tetramic acid [J].
Dixon, DJ ;
Ley, SV ;
Longbottom, DA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (16) :2231-2232
[7]  
GOSSAUER A, 2003, PROGR CHEM ORG NATUR, V86
[8]  
Höltzel A, 2000, ANGEW CHEM INT EDIT, V39, P2766
[9]   SYNTHESEN MIT ENAMINEN .X. SYSTEMATISCHE SYNTHESE METHYLVERZWEIGTER CARBONSAUREN [J].
HUNIG, S ;
SALZWEDE.M .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (03) :823-&
[10]   SYNTHESEN MIT ENAMINEN .9. KETTENVERLANGERUNG DER DELTA10-UNDECENSAURE UM 5 UND 6 C-ATOME [J].
HUNIG, S ;
ECKARDT, W .
CHEMISCHE BERICHTE-RECUEIL, 1962, 95 (10) :2493-&