Indole arylation studies directed towards the synthesis of simplified eastern subunits of chloropeptin and kistamycin

被引：23

作者：

Carbonnelle, AC ^{[1
]}

Zamora, EG ^{[1
]}

Beugelmans, R ^{[1
]}

Roussi, G ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 25期

关键词：

D O I：

10.1016/S0040-4039(98)00818-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl indoles which are building blocks for the synthesis of simplified analogues of macropolypeptides containing an endo carbon-carbon bond are obtained by Suzuki Pd-catalyzed cross coupling reactions involving either haloindoles or indole boronic acids and properly meta substituted phenyl components. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：4467 / 4470

页数：4

共 14 条

[1] Trifluoromethanesulfonic anhydride-4-(N,N-dimethylamino)pyridine as a reagent combination for effecting Bischler-Napieralski cyclisation under mild conditions: Application to total syntheses of the Amaryllidaceae alkaloids N-methylcrinasiadine, anhydrolycorinone, hippadine and oxoassoanine [J].

Banwell, MG ;

Bissett, BD ;

Busato, S ;

Cowden, CJ ;

Hockless, DCR ;

Holman, JW ;

Read, RW ;

Wu, AW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (24) :2551-2553

[2] The first synthesis of 16+15-membered bicyclic polypeptide model of A-O-C-B-O-D rings of kistamicin [J].

Beugelmans, R ;

Zamora, EG ;

Roussi, G .

TETRAHEDRON LETTERS, 1997, 38 (47) :8189-8192

[3] HIGH YIELDS OF UNSYMMETRICAL BIARYLS VIA CROSS-COUPLING OF ARYLBORONIC ACIDS WITH HALOARENES USING A MODIFIED SUZUKI-BELETSKAYA PROCEDURE [J].

CAMPI, EM ;

JACKSON, WR ;

MARCUCCIO, SM ;

NAESLUND, CGM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (20) :2395-2395

[4]

CARRERA JM, 1994, SYNLETT, P93

[5] N-(ACYLOXYALKYL)PYRIDINIUM SALTS AS SOLUBLE PRODRUGS OF A POTENT PLATELET-ACTIVATING-FACTOR ANTAGONIST [J].

DAVIDSEN, SK ;

SUMMERS, JB ;

ALBERT, DH ;

HOLMS, JH ;

HEYMAN, HR ;

MAGOC, TJ ;

CONWAY, RG ;

RHEIN, DA ;

CARTER, GW .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (26) :4423-4429

[6] Stereostructure of (-)-chloropeptin I, a novel inhibitor of gp120-CD4 binding, via high-temperature molecular dynamics, Monte Carlo conformational searching, and NMR spectroscopy [J].

Gouda, H ;

Matsuzaki, K ;

Tanaka, H ;

Hirono, S ;

Omura, S ;

McCauley, JA ;

Sprengeler, PA ;

Furst, GT ;

Smith, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) :13087-13088

[7] Synthesis of C-C biaryl segment of complestatin and chloropeptin: Approach to the right hand CEF-ring system of complestatin [J].

Gurjar, MK ;

Tripathy, NK .

TETRAHEDRON LETTERS, 1997, 38 (12) :2163-2166

[8] CHLOROPEPTIN-I AND CHLOROPEPTIN-II, NOVEL INHIBITORS AGAINST GP120-CD4 BINDING FROM STREPTOMYCES SP [J].

MATSUZAKI, K ;

IKEDA, H ;

OGINO, T ;

MATSUMOTO, A ;

WOODRUFF, HB ;

TANAKA, H ;

OMURA, S .

JOURNAL OF ANTIBIOTICS, 1994, 47 (10) :1173-1174

[9] METAL-HALOGEN EXCHANGE OF BROMOINDOLES - A ROUTE TO SUBSTITUTED INDOLES [J].

MOYER, MP ;

SHIURBA, JF ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5106-5110

[10] NEW ANTIVIRAL ANTIBIOTICS, KISTAMICIN-A AND KISTAMICIN-B .1. TAXONOMY, PRODUCTION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITIES [J].

NARUSE, N ;

TENMYO, O ;

KOBARU, S ;

HATORI, M ;

TOMITA, K ;

HAMAGISHI, Y ;

OKI, T ;

CAREOFOKUMURA, J .

JOURNAL OF ANTIBIOTICS, 1993, 46 (12) :1804-1811

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