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Synfacts 2008(3): 0263-0263
DOI: 10.1055/s-2008-1042713
DOI: 10.1055/s-2008-1042713
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New YorkShortcut to a 42-Membered Trianglimine Macrocycle
J. Hodaová*, M. Budínsk
Academy of Sciences of the Czech Republic and Institute of Chemical Technology, Prague, Czech Republic
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Februar 2008 (online)

Significance
The authors report the synthesis of a 42-membered trianglimine macrocycle 4. To obtain 2,2′-bipyridine-5,5′-dicarbaldehyde 3, the key compound in their synthetic pathway, the dimethyl-bipyridine 1 was first transformed to 2 using Bredereck’s reagent. Subsequent oxidative cleavage led to the formation of 3 in 72% yield. The following [3+3] cyclocondensation afforded 4 as the only product in 84% yield after 24 hours at room temperature.