A concise synthesis of topsentin A and nortopsentins B and D

被引:56
作者
Miyake, FY [1 ]
Yakushijin, K [1 ]
Horne, DA [1 ]
机构
[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA
关键词
D O I
10.1021/ol000124g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A concise synthesis of topsentin A (R-1 = R-2 = H) and nortopsentins B (R-1 = Br, R2 = H) and D (R-1 = R-2 = H) is described from oxotryptamine 5 via reduction of acyl cyanide 4, Regiospecific bromination of a cyanoindole afforded 6-bromo-3-cyanoindole (10) as the major product.
引用
收藏
页码:2121 / 2123
页数:3
相关论文
共 21 条
[1]   A three-component coupling approach to the marine bis-indole alkaloids: Topsentin, deoxytopsentin and bromotopsentin [J].
Achab, S .
TETRAHEDRON LETTERS, 1996, 37 (31) :5503-5506
[2]   Synthesis of a bis-pyrrolo-quinone structure analogue to wakayin [J].
Barret, R ;
Roue, N .
TETRAHEDRON LETTERS, 1999, 40 (20) :3889-3890
[3]   TOPSENTINS, NEW TOXIC BIS-INDOLE ALKALOIDS FROM THE MARINE SPONGE TOPSENTIA-GENITRIX [J].
BARTIK, K ;
BRAEKMAN, JC ;
DALOZE, D ;
STOLLER, C ;
HUYSECOM, J ;
VANDEVYVER, G ;
OTTINGER, R .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (09) :2118-2121
[4]   SPONGE SECONDARY METABOLITES - NEW RESULTS [J].
BRAEKMAN, JC ;
DALOZE, D ;
MOUSSIAUX, B ;
STOLLER, C ;
DENEUBOURG, F .
PURE AND APPLIED CHEMISTRY, 1989, 61 (03) :509-512
[5]  
CLARK RD, 1984, HETEROCYCLES, V22, P195
[6]   Syntheses and biological activities of bis(3-indolyl)thiazoles, analogues of marine bis(indole)alkaloid nortopsentins [J].
Gu, XH ;
Wan, XZ ;
Jiang, B .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (04) :569-572
[7]  
HOGAN IT, 1984, TETRAHEDRON, V40, P81
[8]   THE CHEMISTRY OF ACYL CYANIDES [J].
HUNIG, S ;
SCHALLER, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (01) :36-49
[9]   SUCCESSIVE DIARYLATION AT THE CARBON POSITIONS (2/4 AND 2/5) OF 1H-IMIDAZOLE AND ITS APPLICATION TO THE TOTAL SYNTHESIS OF NORTOPSENTIN-D [J].
KASWASAKI, I ;
YAMASHITA, M ;
OHTA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) :2085-2086
[10]  
Kawasaki I, 1996, CHEM PHARM BULL, V44, P1831