Cultivation and extraction of the
fungus Talaromyces stipitatus led to the isolation
of five new oxyphenalenone–amino acid
hybrids, which were named talauxins E, Q, V, L, and I based on the
corresponding one-letter amino acid codes, along with their putative
biosynthetic precursor, duclauxin. The rapid reaction of duclauxin
with amino acids to produce talauxins was demonstrated in vitro and
exploited to generate a small library of natural and unnatural talauxins.
Talauxin V was shown to undergo spontaneous elimination of methyl
acetate to yield the corresponding neoclauxin scaffold. This process
was modeled using density functional theory calculations, revealing
a dramatic change in conformation resulting from the syn elimination of methyl acetate.