When a healthy and balanced diet is not achieved, nutritional supplements are used to help deal with the resulting health issues and enhance the body's performance. Two compounds of interest in this research, ketone bodies and β-Hydroxy β-Methylbutyrate (HMB) have been used for dealing with the side effects of various health conditions including muscle mass loss and insufficient food intake. Although these molecules have been used extensively as supplements, no supplement was found which combined the properties of both ketone bodies and HMB. This project was conceived to create a novel category of molecules that combine the properties of both ketone bodies and HMB that can be used as supplements for treating a wide range of health-related issues. Acetoacetate and isopentyldiol were used as the sources of ketone bodies and HMB, respectively. Six novel compounds were synthesized using transesterification of acetoacetate and isopentyldiol. Some of the developed reaction procedures were versatile as they could be performed under a variety of parameters such as solventless, catalyst-free, and mild conditions. Immobilized enzymes and chemicals were used to generate new compounds under greener parameters. The compounds that were isolated were characterized using GCMS, H NMR, and FTIR instrumentation. In summary, the goal of this research project was to design and synthesize novel ketone body analogs.