Two Syntheses of the 16- and 17-Membered DEF Ring Systems of Chloropeptin and Complestatin

Two syntheses of a model system of the DEF ring system of complestatin and chloropeptin are described. The key step in both of these syntheses involves the formation of the biaryl linkage using a palladium-catalyzed Suzuki cross-coupling reaction and a catalytic enantioselective ene reaction to form...

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Bibliographic Details
Published inOrganic letters Vol. 1; no. 9; pp. 1443 - 1446
Main Authors Elder, Amy M, Rich, Daniel H
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.11.1999
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Chlorophenols - chemical synthesis
Chlorophenols - chemistry
Molecular Structure
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Peptides, Cyclic
Physical Sciences
Science & Technology
FERMENTATION
STREPTOMYCES SP
COMPLEMENT
INHIBITING GP120-CD4 BINDING
ESTERS
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Summary:Two syntheses of a model system of the DEF ring system of complestatin and chloropeptin are described. The key step in both of these syntheses involves the formation of the biaryl linkage using a palladium-catalyzed Suzuki cross-coupling reaction and a catalytic enantioselective ene reaction to form the 6-bromo-d-tryptophan. Additionally, ring contraction of the 17-membered DEF ring system of complestatin generates the 16-membered DEF ring system of chloropeptin in a biomimetic fashion.
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol990990x