@article {46324, title = {Access to a stereoisomer library of solomonamide macrocycles}, journal = {Chemistry-An Asian Journal}, year = {2019}, month = {OCT}, type = {Article; Early Access}, abstract = {

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.

}, keywords = {Crotylation, Heck reaction, Inflammation, Macrocycles, Stereochemistry}, issn = {1861-4728}, doi = {10.1002/asia.201901075}, author = {Jachak, Gorakhnath R. and Athawale, Paresh R. and Choudhury, Rahul and Kashinath, K. and Reddy, D. Srinivasa} }