Intramolecular O-Arylation of Phenols with Phenylboronic Acids:  Application to the Synthesis of Macrocyclic Metalloproteinase Inhibitors

The copper acetate mediated intramolecular O-arylation of phenols with phenylboronic acid pseudopeptides is the key step in the preparation of macrocyclic biphenyl ether hydroxamic acid inhibitors of collagenase 1 and gelatinases A and B. The intramolecular macrocyclization was found to be mild and...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 3; no. 7; pp. 1029 - 1032
Main Authors Decicco, Carl P, Song, Ying, Evans, David A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.04.2001
Amer Chemical Soc
Subjects
Boronic Acids - chemistry
Chemistry
Chemistry, Organic
Collagenases
Copper - chemistry
Cyclization
Drug Design
Humans
Matrix Metalloproteinase Inhibitors
Molecular Structure
Phenols - chemistry
Physical Sciences
Protease Inhibitors - chemical synthesis
Protease Inhibitors - chemistry
Science & Technology
CUPRIC ACETATE
MATRIX METALLOPROTEINASES
CONVERTING ENZYME
DESIGN
PEPTIDES
FERMENTATION
HIV-1 PROTEASE
BINDING
HALOPHYTICA SUBSP EXILISIA
AMINOPEPTIDASE-B
Online AccessGet full text

Cover

More Information
Summary:The copper acetate mediated intramolecular O-arylation of phenols with phenylboronic acid pseudopeptides is the key step in the preparation of macrocyclic biphenyl ether hydroxamic acid inhibitors of collagenase 1 and gelatinases A and B. The intramolecular macrocyclization was found to be mild and tolerant of common chemical functionality. This methodology should provide a general route to macrocyclic biphenyl ethers.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol015572i