Discoveries from the Abyss: The Abyssomicins and Their Total Synthesis

Abyssomicin C is a recently discovered antibiotic with promising antibacterial activity, high structural complexity, and a novel mechanism of action. We give an account of our abyssomicin campaign and some of the discoveries that were borne of our total synthesis efforts, including a new Lewis acid templated Diels Alder reaction, the previously undescribed atrop-abyssomicin C, a facile Bronsted acid-catalyzed isomerization of abyssomicin C, and clarification of the likely biosynthetic origin of abyssomicin D.