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Published on: March 20, 2017
Regioselective Synthesis of Substituted Cyclopenta[l]phenanthrenes
David M Connors1, Nancy S Goroff1
1Department of Chemistry, Stony Brook University , Stony Brook, New York 11794-3400, United States.
Abstract:
A simple and efficient synthesis of cyclopenta[l]phenanthrenes from substituted acetophenones provides access to polycyclic aromatics with a variety of substitution patterns. The synthesis requires only three steps from a silyl enol ether: a Mukaiyama aldol reaction followed by McMurry coupling and then Mallory photocyclooxidation to give the target phenanthrenes. Photocyclization conditions have been found that give regioselective formation of 2,7-phenanthrenes from bis(meta-substituted) stilbenes.
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