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Access to a Stereoisomer Library of Solomonamide Macrocycles
Author(s) -
Jachak Gorakhnath R.,
Athawale Paresh R.,
Choudhury Rahul,
Kashinath K.,
Reddy D. Srinivasa
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201901075
Subject(s) - intramolecular force , aldol reaction , peptide , stereochemistry , chemistry , fragment (logic) , reagent , combinatorial chemistry , substrate (aquarium) , heck reaction , ligand (biochemistry) , computer science , palladium , organic chemistry , catalysis , receptor , biochemistry , programming language , biology , ecology
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.