Siloxane-Based Cross-Coupling of Bromopyridine Derivatives:  Studies for the Synthesis of Streptonigrin and Lavendamycin

Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes to give sterically demanding biaryls. The 3-nitro-4-bromopyridine derivative coupled in good yield with TBAT (tetrabutylammonium triphenyldifluorosilicat...

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Bibliographic Details
Published inOrganic letters Vol. 5; no. 25; pp. 4779 - 4782
Main Authors McElroy, William T, DeShong, Philip
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.12.2003
Amer Chemical Soc
Subjects
Antibiotics, Antineoplastic - chemical synthesis
Chemistry
Chemistry, Organic
Molecular Structure
Physical Sciences
Pyridines - chemical synthesis
Pyridines - chemistry
Science & Technology
Siloxanes - chemistry
Streptonigrin - analogs & derivatives
Streptonigrin - chemical synthesis
CONNECTION
METALATION
FORMAL SYNTHESIS
ANALOGS
STILLE
CONVERGENT SYNTHESIS
EFFICIENT
METHYL-ESTER
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Summary:Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes to give sterically demanding biaryls. The 3-nitro-4-bromopyridine derivative coupled in good yield with TBAT (tetrabutylammonium triphenyldifluorosilicate) to provide a biaryl adduct that serves as a model system for the total synthesis of the antitumor antibiotics streptonigrin and lavendamycin.
Bibliography:Medline
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ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0357503