Premium
Synthesis of Complex and Diverse Compounds through Ring Distortion of Abietic Acid
Author(s) -
Rafferty Ryan J.,
Hicklin Robert W.,
Maloof Katherine A.,
Hergenrother Paul J.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201308743
Subject(s) - abietic acid , stereocenter , natural product , chemistry , ring (chemistry) , molecule , combinatorial chemistry , abietane , stereochemistry , organic chemistry , nanotechnology , rosin , resin acid , materials science , diterpene , catalysis , enantioselective synthesis
Many compound screening collections are populated by members that possess a low degree of structural complexity. In an effort to generate compounds that are both complex and diverse, we have developed a strategy that uses natural products as a starting point for complex molecule synthesis. Herein we apply this complexity‐to‐diversity approach to abietic acid, an abundant natural product used commercially in paints, varnishes, and lacquers. From abietic acid we synthesize a collection of complex (as assessed by fraction of sp 3 ‐hybridized carbons and number of stereogenic centers) and diverse (as assessed by Tanimoto analysis) small molecules. The 84 compounds constructed herein, and those created through similar efforts, should find utility in a variety of biological screens.