Polycyclic polyprenylated acylphloroglucinols (PPAPs) comprise a class of biologically active secondary metablites. The antidepressant, antioxidant, antiviral, anti HIV and anticancer biological activities of PPAPs has attracted more and more attention in recent years. More and more people have become interested in their ability to modulate the action of neurotransmitters associated with depression and related CNS (central nervous system) damages.

Garsubellin A, isolated from Garcinia subelliptica, is a potent inducer of choline acetyltransferase and might thus be a promising pharmaceutical lead for the development of agents for treating Alzheimer’s disease. Several approaches to garsubellin A that other research groups have employed are discussed.

Our own synthetic efforts toward an enantioselective total synthesis of garsubellin A via three different strategies: (1) claisen rearrangement, (2) reductive alkylation, and (3) direct alkynylation are discussed. The methodologies developed during the investigation in order to build up all carbon quaternary centers are also discussed, including reductive alkylation and alkynylation.