Donghua Dai, B. Venepalli
May 6, 2015
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Journal
Tetrahedron Letters
Abstract
Abstract ortho -Lithiation of N-Boc-3-bromopyrroles ( 7b , 7d ) with LDA in THF at −75 °C, followed by reactions with ethyl formate gave exclusive C2-formylpyrroles ( 9b , 9c , 9d , 9e ) in good yields. This methodology was applied to the synthesis of 3-(2-formyl-4-methyl-1- H -pyrrol-3-yl)propanoic acid ( 4a ), a penultimate precursor to SU5402 . The process for making 4a has also been optimized which involves a non-chromatography eight-step synthesis with an overall 18% yield.