Regioselective intramolecular reactions of 2-indolylacyl radicals with pyridines: a direct synthetic entry to ellipticine quinones.
[reaction: see text] 2-Indolylacyl radicals generated from the corresponding selenoesters under hexabutylditin-hnu conditions undergo regioselective intramolecular reaction with unprotonated pyridines to give polycyclic indolylpyridyl ketones. For substrates bearing a (3-pyridyl)methyl moiety connected to the 3-position of the indole ring, the cyclization provides easy access to ellipticine quinones.
Bennasar
M-Lluïsa
ML
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Spain. bennasar@ub.edu
Roca
Tomàs
T
Ferrando
Francesc
F
D003500:Cyclization; D004611:Ellipticines / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D005609:Free Radicals; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D011809:Quinones / Q000138:chemical synthesis / Q000737:chemistry*; D012643:Selenium / Q000737:chemistry
D004611:Ellipticines; D004952:Esters; D005609:Free Radicals; D007211:Indoles; D011725:Pyridines; D011809:Quinones; C034192:ellipticine; D012643:Selenium