Fischer indolization of 2-sulfonyloxyphenylhydrazones: A new and practical approach for preparing 7-oxygenated indoles and application to the first synthesis of eudistomidin-A (Fischer indolization and its related compounds, Part 28)

被引:25
作者
Murakami, Y
Watanabe, T
Takahashi, H
Yokoo, H
Nakazawa, Y
Koshimizu, H
Adachi, N
Kurita, M
Yoshino, T
Inagaki, T
Ohishi, M
Watanabe, M
Tani, M
Yokoyama, Y
机构
[1] Toho Univ, Sch Pharmaceut Sci, Funabashi, Chiba 274, Japan
[2] Chiba Univ, Fac Pharmaceut Sci, Inage Ku, Chiba 263, Japan
关键词
D O I
10.1016/S0040-4020(97)10255-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for synthesis of 7-oxygenated indoles was established by Fischer indolization of the phenylhydrazones (10) with a sulfonyloxy group at the ortho-position. This method was applied to the first synthesis of the calmodulin antagonist eudistomidin-A (2). (C) 1997 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:45 / 64
页数:20
相关论文
共 29 条
[1]  
Ainsworth C., 1963, ORG SYNTH, V4, P536
[2]  
ALVAREZ EF, 1969, B SOC CHIM FR, P1932
[3]  
[Anonymous], 1973, ORG SYNTH COLL
[4]   THE FISCHER INDOLE SYNTHESIS .1. [J].
BARNES, CS ;
PAUSACKER, KH ;
SCHUBERT, CI .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (JUN) :1381-1384
[5]  
Batcho A. D., U. S. Patent, Patent No. [3,976,639, 3976639]
[6]   SYNTHESIS OF BENZOFURANS FROM OXYGENATED PHENOXYAMINES [J].
CASTELLINO, AJ ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23) :4399-4404
[7]  
CRUM JD, 1966, J CHEM SOC CHEM COMM, P417
[8]   ISOLATION AND CHARACTERIZATION OF PDE-I AND PDE-II, INHIBITORS OF CYCLIC ADENOSINE-3',5'-MONOPHOSPHATE PHOSPHODIESTERASE [J].
ENOMOTO, Y ;
FURUTANI, Y ;
NAGANAWA, H ;
HAMADA, M ;
TAKEUCHI, T ;
UMEZAWA, H .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1978, 42 (07) :1331-1336
[9]  
FARBENID IG, 1937, Patent No. 650999
[10]  
Fraude G, 1878, BER DTSCH CHEM GES, V11, P2189