Regioselective Synthesis of Substituted Cyclopenta[l]phenanthrenes.

Org Lett

Department of Chemistry, Stony Brook University, Stony Brook, New York 11794-3400, United States.

Published: September 2016


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Article 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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http://dx.doi.org/10.1021/acs.orglett.6b02008DOI Listing

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