UC San Diego

This thesis presents the total synthesis of the natural product acremolin and its structural reassignment along with attempts towards synthesizing analogues of natural product. Acremolin is a natural product reported as a 1H- azirine-containing guanine derivative isolated from Acremonium strictum. Due to the known structural instability of 1H-azirines systems, the original assignment is highly improbable. Two alternative structures were proposed based on the evaluation of spectroscopic data reported for the natural product. Both isomers were synthesized from guanine and the structure of the natural product was reassigned as N², 3-etheno-2'- isopropyl-1-methylguanine based on matching spectroscopic data. Analogues of the natural product were then synthesized and investigated for potential cytotoxic activity