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Paper | Special issue | Vol 88, No. 2, 2014, pp.1275-1285
Published online, 7th August, 2013
DOI: 10.3987/COM-13-S(S)90
Regioselective Bromination: An Approach to the D-Ring of the Gilvocarcins

Ehesan U. Sharif and George A. O'Doherty*

*Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA 02115-5096, U.S.A.


A method for the regioselective ortho-bromination of unsymmetrically protected 3,5-dihydroxybenzoic acid esters has been developed. The route involves protecting group optimization studies to attain high regioselectivity for the ortho-bromination. Pd-catalyzed stannation and boration were performed to construct the D-ring coupling partners for the synthesis of gilvocarcin analogs.