Two total syntheses of the potent protein kinase C inhibitory fungal m
etabolite balanol are described. In the first approach, the core amino
hydroxyazepane subunit was prepared in racemic form by stereospecific
functionalization of N-benzyl-epsilon-caprolactam. Resolution prior to
coupling to the benzophenone subunit provided access to both enantiom
ers of balanol. In the second approach, an efficient silicon-mediated
cyclization of(2S,3R)-3-hydroxylysine followed by reduction provided t
he azepane subunit in enantiomerically pure form. The sterically conge
sted benzophenone subunit was assembled from two highly substituted ar
omatic precursors by way of an anionic home-Fries rearrangement.