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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| Published in | Organic letters Vol. 5; no. 25; pp. 4779 - 4782 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
11.12.2003
Amer Chemical Soc |
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| Abstract | 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. |
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| AbstractList | 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. 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. [reaction: see text] [GRAPHICS] 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 triphenyidifluorosilicate) to provide a biaryl adduct that serves as a model system for the total synthesis of the antitumor antibiotics streptonigrin and lavendamycin. |
| Author | DeShong, Philip McElroy, William T |
| Author_xml | – sequence: 1 givenname: William T surname: McElroy fullname: McElroy, William T – sequence: 2 givenname: Philip surname: DeShong fullname: DeShong, Philip |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/14653672$$D View this record in MEDLINE/PubMed |
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| Snippet | Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes to give... [GRAPHICS] Highly functionalized 4-bromopyridines were prepared and found to undergo fluoride-promoted, Pd-catalyzed cross-coupling with aryltrialkoxysilanes... |
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| SubjectTerms | 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 |
| Title | Siloxane-Based Cross-Coupling of Bromopyridine Derivatives: Studies for the Synthesis of Streptonigrin and Lavendamycin |
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