UC San Diego

Decalin-containing natural products along with tetramic acid moieties present characteristic functionalities for antibiotic and antifungal activity. Thus, the total synthesis of a natural product in this class was determined to be of importance in a world where antibiotic resistance is an ever-growing issue. This creates the need to consistently develop novel antibiotics that can effectively attack various targets that are essential to the microorganism’s survival. Exploring the total synthesis of Conipyridoin analogs, which are decalin and tetramic acid-containing natural products, was carried out in this paper in 12 efficient steps. Major transformations in this synthesis include the creation of the decalin moiety through a Lewis acid-mediated intramolecular Diels Alder reaction along with a Lacey-Dieckmann condensation with an amino acid to build the tetramic acid core. This biomimetic synthesis allows for similar analogs of Conipyridoin to be synthesized with ease.