Total synthesis of marine bisindole alkaloids, (+)-hamacanthins A, B and (-)-antipode of cis-dihydrohamacanthin B

被引:60
作者
Kouko, T [1 ]
Matsumura, K [1 ]
Kawasaki, T [1 ]
机构
[1] Meiji Pharmaceut Univ, Tokyo 2048588, Japan
关键词
bromoindole; indolylglycinol; oxazolidin-2-one; absolute configuration;
D O I
10.1016/j.tet.2005.01.058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of the marine bisindole alkaloids, (+)-hamacanthins A (2a) and B (2b), and (-)-antipode of cis-dihydrohamacanthin B (2e) was achieved by transamidation-cyclization of N-(2-aminoethyl)-2-oxoethanamide 18 derived from (S)-indolylglycinol 10. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2309 / 2318
页数:10
相关论文
共 24 条
[1]   Dragmacidins:: New protein phosphatase inhibitors from a southern Australian deep-water marine sponge, Spongosorites sp. [J].
Capon, RJ ;
Rooney, F ;
Murray, LM ;
Collins, E ;
Sim, ATR ;
Rostas, JAP ;
Butler, MS ;
Carroll, AR .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (05) :660-662
[2]   New bisindole alkaloids of the topsentin and hamacanthin classes from the Mediterranean marine sponge Rhaphisia lacazei [J].
Casapullo, A ;
Bifulco, G ;
Bruno, I ;
Riccio, R .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (04) :447-451
[3]   Dragmacidin F:: A new antiviral bromoindole alkaloid from the mediterranean sponge Halicortex sp. [J].
Cutignano, A ;
Bifulco, G ;
Bruno, I ;
Casapullo, A ;
Gomez-Paloma, L ;
Riccio, R .
TETRAHEDRON, 2000, 56 (23) :3743-3748
[4]   6-BROMOTRYPTAMINE DERIVATIVES FROM THE GULF OF CALIFORNIA TUNICATE DIDEMNUM-CANDIDUM [J].
FAHY, E ;
POTTS, BCM ;
FAULKNER, DJ ;
SMITH, K .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (02) :564-569
[5]   The total synthesis of (+)-dragmacidin F [J].
Garg, NK ;
Caspi, DD ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) :9552-9553
[6]   The first total synthesis of dragmacidin D [J].
Garg, NK ;
Sarpong, R ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13179-13184
[7]   HAMACANTHIN-A AND HAMACANTHIN-B, NEW ANTIFUNGAL BIS INDOLE ALKALOIDS FROM THE DEEP-WATER MARINE SPONGE, HAMACANTHA SP [J].
GUNASEKERA, SP ;
MCCARTHY, PJ ;
KELLYBORGES, M .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (10) :1437-1441
[8]   Enantioselective synthesis of marine indole alkaloid hamacanthin B [J].
Jiang, B ;
Yang, CG ;
Wang, J .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1396-1398
[9]   Enantioselective synthesis for the (-)-antipode of the pyrazinone marine alkaloid, hamacanthin A [J].
Jiang, B ;
Yang, CG ;
Wang, J .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) :4865-4869
[10]   TOTAL SYNTHESIS OF (+/-)-DRAGMACIDIN - A CYTOTOXIC BIS(INDOLE)ALKALOID OF MARINE ORIGIN [J].
JIANG, B ;
SMALLHEER, JM ;
AMARALLY, C ;
WUONOLA, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) :6823-6827