Regiocontrol by Remote Substituents. A Direct Total Synthesis of Racemic Hongconin

George A. Kraus, Iowa State University
Jun Li, Iowa State University
Mark S. Gordon, Iowa State University
Jan H. Jensen, Iowa State University

Reprinted (adapted) with permission from Journal of Organic Chemistry 59 (1994): 2219, doi:10.1021/jo00087a044. Copyright 1994 American Chemical Society.

Abstract

The total synthesis of hongconin (1) has been completed. Key steps include the metalation of a benzylic alcohol, the formation of a six-membered ring ether via a mercury-mediated cyclization, and the regioselective installation of the naphthalene ring by way of a Diels-Alder reaction.