APPLICATION OF THE SUZUKI BIPHENYL SYNTHESIS TO THE NATURAL-PRODUCTS BIPHENOMYCIN AND VANCOMYCIN

被引：56

作者：

BROWN, AG ^{[1
]}

CRIMMIN, MJ ^{[1
]}

EDWARDS, PD ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,DIV RES,BROCKHAM PK,BETCHWORTH RH3 7AJ,SURREY,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 01期

关键词：

D O I：

10.1039/p19920000123

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the unsymmetrical biphenyls 10 and 25 has been carried out by the palladium(0) catalysed coupling of the aryl boronic acid derivatives 5 and 20 with the aryl bromides 9 and 23 derived from (R)-4-hydroxyphenylglycine and (S)-tyrosine. In the former case unsuccessful attempts were made to bring about cyclization to compound 4 which is an analogue of the biphenyl ring system found in vancomycin. In the latter case, a variety of cyclization methods were used to give the cyclic products 34 and 35 which are analogues of the biphenomycin antibiotics.

引用

页码：123 / 130

页数：8

共 19 条

[11] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS
MITSUNOBU, O
[J]. SYNTHESIS-STUTTGART, 1981, (01): : 1 - 28
[12] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF PHENYLBORONIC ACID WITH HALOARENES IN THE PRESENCE OF BASES
MIYAURA, N
YANAGI, T
SUZUKI, A
[J]. SYNTHETIC COMMUNICATIONS, 1981, 11 (07) : 513 - 519
[13] AMINO-ACIDS AND PEPTIDES .72. SYNTHESIS OF (S,S)-DIISOTYROSINE AND ITS INCORPORATION IN AN ANSA TRIPEPTIDE
SCHMIDT, U
MEYER, R
LEITENBERGER, V
LIEBERKNECHT, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (07): : 929 - 930
[14] SYNTHESIS OF PEPTIDE ALKALOIDS .5. NEW METHOD FOR SYNTHESIS OF ANSA PEPTIDES - AMINO-ACIDS AND PEPTIDES .34.
SCHMIDT, U
LIEBERKNECHT, A
GRIESSER, H
TALBIERSKY, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (17) : 3261 - 3264
[15] THE SYNTHESIS OF BIPHENOMYCIN-B
SCHMIDT, U
MEYER, R
LEITENBERGER, V
LIEBERKNECHT, A
GRIESSER, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (05) : 275 - 277
[16] SYNTHETIC CONNECTIONS TO THE AROMATIC DIRECTED METALATION REACTION - FUNCTIONALIZED ARYL BORONIC ACIDS BY IPSO BORODESILYLATION - GENERAL SYNTHESES OF UNSYMMETRICAL BIPHENYLS AND META-TERPHENYLS
SHARP, MJ
CHENG, W
SNIECKUS, V
[J]. TETRAHEDRON LETTERS, 1987, 28 (43) : 5093 - 5096
[17] SYNTHETIC CONNECTIONS TO THE AROMATIC DIRECTED METALATION REACTION - UNSYMMETRICAL BIARYLS BY PALLADIUM-CATALYZED CROSS COUPLING OF DIRECTED METALATION-DERIVED ARYLBORONIC ACIDS WITH ARYL HALIDES
SHARP, MJ
SNIECKUS, V
[J]. TETRAHEDRON LETTERS, 1985, 26 (49) : 5997 - 6000
[18] SYNTHESIS OF AROMATIC BORONIC ACIDS - ALDEHYDO BORONIC ACIDS AND A BORONIC ACID ANALOG OF TYROSINE
SNYDER, HR
REEDY, AJ
LENNARZ, WJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (04) : 835 - 838
[19] BIPHENOMYCIN-A AND BIPHENOMYCIN-B, NOVEL PEPTIDE ANTIBIOTICS .2. STRUCTURAL ELUCIDATION OF BIPHENOMYCIN-A AND BIPHENOMYCIN B
UCHIDA, I
SHIGEMATSU, N
EZAKI, M
HASHIMOTO, M
AOKI, H
IMANAKA, H
[J]. JOURNAL OF ANTIBIOTICS, 1985, 38 (11) : 1462 - 1468

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