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 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]
McElroy
William T
WT
Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.
DeShong
Philip
P
D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*; D012833:Siloxanes / Q000737:chemistry*; D013308:Streptonigrin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D000903:Antibiotics, Antineoplastic; D011725:Pyridines; D012833:Siloxanes; D013308:Streptonigrin; C034566:lavendamycin