Balanol ((-)-1) is a potent protein kinase inhibitory natural product isolated from the fungus Verticillium balanoides. The presence of an ester functionality in this molecule has prompted concern over the metabolic stability of balanol, and has led to a search for active analogs lacking this moiety. The synthesis and serum stability for some of these is presented herein. Balanol ((-)-1) is a potent protein kinase C (PKC) inhibitory natural product isolated from the fungus Verticillium balanoides. PKC is a family of phospholipid-dependent serine/threonine-specific protein kinases involved in cellular growth control, regulation, and differentiation. Activation of PKC is a key step in processes such as cellular proliferation and gene expression, and the enzyme has been implicated in the progress of a number of diseases. The presence of an ester functionality has prompted concern over the metabolic stability of the compound, and has led to a search for active analogs with linking groups other than esters. Completion of the total synthesis of balanol has facilitated the preparation of analogs in which the ester group has been replaced with functionality less susceptable to metabolic degradation. These have included the corresponding amide and ether derivatives. An increase in the steric demands of the ester would be expected to increase resistance to esterases; thus, the tertiary alcohol ester 6 was also prepared. PKC isozyme inhibition data are summarized in Table 1.