Regioselective 6-endo cyclizations of 2-indolylacyl radicals: total synthesis of the pyrido[4,3-b]carbazole alkaloid guatambuine.
A regioselective 6-endo reductive cyclization of 2-indolylacyl radicals constitutes the key step of a straightforward synthetic entry to the olivacine skeleton, illustrated by a total synthesis of the tetrahydropyridine alkaloid guatambuine.
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Barcelona 08028, Spain. bennasar@ub.edu
M-Lluïsa
ML
Bennasar
Tomàs
T
Roca
Francesc
F
Ferrando
D000470:Alkaloids / Q000138:chemical synthesis*; D003500:Cyclization; D004611:Ellipticines / Q000138:chemical synthesis; D005609:Free Radicals; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D007211:Indoles / Q000737:chemistry
D000470:Alkaloids; D004611:Ellipticines; D005609:Free Radicals; D026121:Indole Alkaloids; D007211:Indoles; C515345:guatambuine; C011521:olivacine