Protein Kinase C (PKC) represents an important regulatory element in the signal transduction pathways of mammalian cells. Research interest has increased enormously since the discovery that PKC plays critical roles in cell differentiation, tumor promotion, oncogenesis and cell regulatory processes. The primary driving force of this project was the study and development of enantioselective PKC inhibitors. To accomplish this objective the four stereoisomers, (2S/4S)-, (2RI4S)-, (2R14R)-, and (2S/4R)-6-N,N-dimethyl-2-methyl-2-oxo-l,3-dioxa- 4-pentadecyl-6-aza-2-phosphacyclooctane bromides (la-d) were synthesized and evaluated. Long-alkyl chain optically pure epoxides, the key intermediates for the synthesis, were prepared from relatively inexpensive glyceraldehyde surrogates. Several other intermediates exhibited other biological responses including spermicidal, anti-HIV, mycobactericidal, and anti-cancer activities. / Ph. D.