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
[11]   ENAZIDES .3. THERMOLYSIS OF ALPHA-AZIDOCINNAMATES - SYNTHESIS OF INDOL CARBOXYLATES [J].
HEMETSBE.H ;
KNITTEL, D ;
WEIDMANN, H .
MONATSHEFTE FUR CHEMIE, 1970, 101 (01) :161-&
[12]  
HINO T, 1989, CHEM PHARM BULL, V37, P2596
[13]   The 3-halogeno-2-,-4-, and-6-amino-phenols [J].
Hodgson, HH ;
Kershaw, A .
JOURNAL OF THE CHEMICAL SOCIETY, 1928, :2703-2705
[14]  
ISHII H, 1974, CHEM PHARM BULL, V22, P1981
[15]   FISCHER INDOLIZATION AND ITS RELATED COMPOUNDS .7. DEVELOPMENT OF ABNORMAL FISCHER INDOLIZATION OF ORTHO-METHOXYPHENYLHYDRAZONE TO PROVIDE A SYNTHETIC METHOD FOR USEFUL INDOLE-DERIVATIVES POSSESSING AN ACTIVE METHINE GROUP AT C6 AND NOVEL 3,6'-BIINDOLE DERIVATIVES [J].
ISHII, H ;
MURAKAMI, Y ;
FURUSE, T ;
HOSOYA, K ;
TAKEDA, H ;
IKEDA, N .
TETRAHEDRON, 1973, 29 (14) :1991-2003
[16]   FISCHER INDOLIZATION AND ITS RELATED COMPOUNDS .5. INDOLIZATION OF ETHYL PYRUVATE 2-METHOXYPHENYLHYDRAZONE AND ITS N-METHYL DERIVATIVE WITH PROTIC ACIDS - UNPREDICTABLE PRODUCTS AND MECHANISM [J].
ISHII, H ;
MURAKAMI, Y ;
HOSOYA, K ;
TAKEDA, H ;
SUZUKI, Y ;
IKEDA, N .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1973, 21 (07) :1481-1494
[17]   EUDISTOMIDIN-A, A NOVEL CALMODULIN ANTAGONIST FROM THE OKINAWAN TUNICATE EUDISTOMA-GLAUCUS [J].
KOBAYASHI, J ;
NAKAMURA, H ;
OHIZUMI, Y ;
HIRATA, Y .
TETRAHEDRON LETTERS, 1986, 27 (10) :1191-1194
[18]  
Lazier W. A., 1943, ORG SYN COLL, VII, P142
[19]   1-2-3-4-TETRAHYDRO-6-HYDROXYCARBAZOLE AND 3-HYDROXYCARBAZOLE [J].
MILNE, AH ;
TOMLINSON, ML .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (JUL) :2789-2791
[20]   SYNTHETIC STUDIES OF INDOLES AND RELATED-COMPOUNDS .17. THE FRIEDEL-CRAFTS ACYLATION OF ETHYL PYRROLE-2-CARBOXYLATE - SCOPE, LIMITATIONS, AND APPLICATION TO SYNTHESIS OF 7-SUBSTITUTED INDOLES [J].
MURAKAMI, Y ;
TANI, M ;
ARIYASU, T ;
NISHIYAMA, C ;
WATANABE, T ;
YOKOYAMA, Y .
HETEROCYCLES, 1988, 27 (08) :1855-1860