Development of a Concise Synthesis of Ouabagenin and Hydroxylated Corticosteroid Analogues

The
natural product ouabagenin is a complex cardiotonic steroid
with a highly oxygenated skeleton. This full account describes the
development of a concise synthesis of ouabagenin, including the evolution
of synthetic strategy to access hydroxyl­ation at the C19 position
of a steroid skeleton. In addition, approaches to install the requisite
butenolide moiety at the C17 position are discussed. Lastly, methodology
developed in this synthesis has been applied in the generation of
novel analogues of corticosteroid drugs bearing a hydroxyl group at
the C19 position.