Yu Lin, Chun-Lung Cho, Chih-Wei Ko
Nov 16, 2012
Citations
0
Influential Citations
41
Citations
Journal
The Journal of organic chemistry
Abstract
A range of phenanthrene derivatives were efficiently synthesized by the palladium-catalyzed annulation of 2,2'-diiodobiphenyls with alkynes. The scope, limitations and regioselectivity of the reaction were investigated. The described method was adopted to synthesize 9,10-dialkylphenanthrenes, sterically overcrowded 4,5-disubstituted phenanthrenes and phenanthrene-based alkaloids. Reactions of highly methoxy-substituted biphenyls with 2-(2-propynyl)pyrrolidine and 2-(2-propynyl)piperidine gave 2-(9-phenanthylmethyl)pyrrolidines and 2-(9-phenanthylmethyl)piperidines, respectively. The products were transformed to phenanthroindolizidine and phenanthroquinolizidine alkaloids by the Pictet-Spengler reaction.