Synthesis of dispacamide from the marine sponge Agelas dispar

被引:46
作者
Lindel, T [1 ]
Hoffmann, H [1 ]
机构
[1] Univ Heidelberg, Inst Pharmazeut Chem, D-69120 Heidelberg, Germany
关键词
D O I
10.1016/S0040-4039(97)10387-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The marine natural product dispacamide (1) has been synthesized for the first time starting from 2-thiohydantoin (2). A facile one pot conversion of alkylidene thiohydantoins to the corresponding 2-iminoimidazolones is described employing tert.-butylhydroperoxide (TBHP) in the presence of aqueous ammonia. (C) 1997 Elsevier Science Ltd.
引用
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页码:8935 / 8938
页数:4
相关论文
共 15 条
[1]  
Attaway D., 1993, MARINE BIOTECHNOLOGY, V1
[2]   Dispacamides, anti-histamine alkaloids from Caribbean Agelas sponges [J].
Cafieri, F ;
Fattorusso, E ;
Mangoni, A ;
TaglialatelaScafati, O .
TETRAHEDRON LETTERS, 1996, 37 (20) :3587-3590
[3]   NEW BROMO-PYRROLE DERIVATIVES FROM SPONGE AGELAS-OROIDES [J].
FORENZA, S ;
MINALE, L ;
RICCIO, R .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (18) :1129-&
[4]   REINVESTIGATION INTO STRUCTURE OF OROIDIN, A BROMOPYRROLE DERIVATIVE FROM MARINE SPONGE [J].
GARCIA, EE ;
BENJAMIN, LE ;
FRYER, RI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (03) :78-79
[5]  
GRIBBLE GW, 1996, FORTSCHR CHEM ORG NA, V68, P137
[6]   APLYSINOPSIN-TYPE ALKALOIDS FROM DENDROPHYLLIA SP, A SCLERACTINIAN CORAL OF THE FAMILY DENDROPHYLLIIDAE OF THE PHILIPPINES - FACILE PHOTOCHEMICAL (Z/E) PHOTOISOMERIZATION AND THERMAL REVERSAL [J].
GUELLA, G ;
MANCINI, I ;
ZIBROWIUS, H ;
PIETRA, F .
HELVETICA CHIMICA ACTA, 1989, 72 (07) :1444-1450
[7]   NOVEL APLYSINOPSIN-TYPE ALKALOIDS FROM SCLERACTINIAN CORALS OF THE FAMILY DENDROPHYLLIIDAE OF THE MEDITERRANEAN AND THE PHILIPPINES - CONFIGURATIONAL-ASSIGNMENT CRITERIA, STEREOSPECIFIC SYNTHESIS, AND PHOTOISOMERIZATION [J].
GUELLA, G ;
MANCINI, I ;
ZIBROWIUS, H ;
PIETRA, F .
HELVETICA CHIMICA ACTA, 1988, 71 (04) :773-782
[8]   HYDANTOINE, THIOHYDANTOINE, GLYKOCYAMIDINE .3. UBER DIE ORIENTIERUNG BEI DER MONOBENZYLIERUNG DES 5.5-DIPHENYL-GLYKOCYAMIDINS [J].
LEMPERT, K ;
BREUER, J ;
LEMPERTSRETER, M .
CHEMISCHE BERICHTE-RECUEIL, 1959, 92 (01) :235-239
[9]  
Lindel T, 1997, LIEBIGS ANN-RECL, P1525
[10]   A CONVENIENT SYNTHESIS OF GUANIDINES FROM THIOUREAS [J].
MARYANOFF, CA ;
STANZIONE, RC ;
PLAMPIN, JN ;
MILLS, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1882-1884