TY - JOUR T1 - Access to a stereoisomer library of solomonamide macrocycles JF - Chemistry-An Asian Journal Y1 - 2019 A1 - Jachak, Gorakhnath R. A1 - Athawale, Paresh R. A1 - Choudhury, Rahul A1 - Kashinath, K. A1 - Reddy, D. Srinivasa KW - Crotylation KW - Heck reaction KW - Inflammation KW - Macrocycles KW - Stereochemistry AB -

In an attempt towards understanding stereo-structure activity relationships (SSARs), we have prepared eight possible stereoisomers of solomonamide macrocycles, in particular, by changing the stereochemical pattern of non-peptide fragment AHMOA. Here, we have demonstrated different ways to construct three contiguous chiral centers present in solomonamide B macrocycle using substrate/reagent-controlled methods. These methods involve Brown crotylation, NHK reaction and Evans aldol addition as key steps to synthesize key non-peptide fragment. Further, these non-peptide fragments were converted to their corresponding macrocycles via ligand-free intramolecular Heck reaction.

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Foreign

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3.698

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