The first total synthesis of neohelmanticins A–D, amino derivatives of the 1,2-dihydroxypropane core and biological evaluation

Abstract A concise total synthesis of neohelmanticins A–D has been accomplished in 15 steps starting from commercially available gallic acid. Swern oxidation conditions, a Grignard reaction, Sharpless kinetic resolution, and regioselective ring opening of an epoxide with lithium aluminum hydride (LAH) are the key features to install the basic core, dihydroxy phenyl propane 2 . One hydroxyl group of this core was esterified with tiglic acid followed by the oxidation and esterification with corresponding acids to yield neohelmanticins A–D.