Novel Diels-Alder-type dimerization of 5-ethenyl-2-phenylsulfanyl-1H-imidazoles and its application to biomimetic synthesis of 12,12′-dimethylageliferin

被引：45

作者：

Kawasaki, I ^{[1
]}

Sakaguchi, N ^{[1
]}

Fukushima, N ^{[1
]}

Fujioka, N ^{[1
]}

Nikaido, F ^{[1
]}

Yamashita, M ^{[1
]}

Ohta, S ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Yamashina Ku, Kyoto 6078414, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(02)00782-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder-type dimerization of various 5-ethenyl-2-phenylsulfanyl-1H-imidazoles provided a novel highly regio- and stereoselective route to the preparation of multifunctionalized 4,5,6,7-tetrahydrobenzimidazoles, the basic skeleton of ageliferin, a biologically active pyrrole-imidazole marine alkaloid. The reaction was applied to the synthesis of 12,12'-dimethylageliferin. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：4377 / 4380

页数：4

共 31 条

[1] Chemical defenses of the Caribbean sponges Agelas wiedenmayeri and Agelas conifera
Assmann, M
Lichte, E
Pawlik, JR
Köck, M
[J]. MARINE ECOLOGY PROGRESS SERIES, 2000, 207 : 255 - 262
[2] DESULFURIZATION WITH NICKEL AND COBALT BORIDE - SCOPE, SELECTIVITY, STEREOCHEMISTRY, AND DEUTERIUM-LABELING STUDIES
BACK, TG
BARON, DL
YANG, KX
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) : 2407 - 2413
[3] BELANGER P, 1979, TETRAHEDRON LETT, P2505
[4] An efficient hetero Diels-Alder approach to imidazo[4,5-c]pyridazines as purine analogues
Deghati, PYF
Wanner, MJ
Koomen, GJ
[J]. TETRAHEDRON LETTERS, 1998, 39 (25) : 4561 - 4564
[5] New bromopyrrole alkaloids from the indopacific sponge Agelas nakamurai
Eder, C
Proksch, P
Wray, V
van Soest, RWM
Ferdinandus, E
Pattisina, LA
Sudarsono
[J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (09): : 1295 - 1297
[6] NEW BROMO-PYRROLE DERIVATIVES FROM SPONGE AGELAS-OROIDES
FORENZA, S
MINALE, L
RICCIO, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (18): : 1129 - &
[7] A convergent approach to midpacamide and dispacamide pyrrole-imidazole marine alkaloids
Fresneda, PM
Molina, P
Sanz, MA
[J]. TETRAHEDRON LETTERS, 2001, 42 (05) : 851 - 854
[8] New access to 1,3-dialkyl-2,3-dihydro-2-imino-1H-imidazoles and their application to the first total synthesis of naamine B, a marine 2,3-dihydro-2-imino-1,3-dimethyl-1H-imidazole alkaloid
Kawasaki, I
Nakamura, S
Kakuno, A
Yamashita, M
Ohta, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (23): : 3095 - 3099
[9] Kawasaki I, 1998, HETEROCYCLES, V48, P1887
[10] Kawasaki I, 1996, HETEROCYCLES, V43, P1375

← 1 2 3 4 →