Synthetic studies on lemonomycin: construction of the tetracyclic core.

Tetrahedron

Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, United States ; University of Colorado Cancer Center, Aurora, Colorado 80045, United States.

Published: September 2013

A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4114395PMC
http://dx.doi.org/10.1016/j.tet.2013.05.009DOI Listing

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