Oleanolic acid (OA) is a pentacyclic triterpenoid class of natural products that possess a broad range of biological activities, specifically anticancer activities. Considering the anticancer potential of OA, a large number of analogs have been prepared by several researchers through modifications at C-3, C-12, and C-28 -COOH to develop potent anticancer agents with improved cytotoxicity and pharmaceutical properties. Some of the synthesized derivatives have been assessed in clinical trials also. This review summarizes the most recent synthetic and biological efforts in the development of oleanolic acid and its analogs during the period from 2017 to 2020. Reports published during this period revealed that both OA and its analogs possess a remarkable potential for the development of effective anticancer agents along with several others, such as anti-inflammatory, anti-viral, antimicrobial, and anti-diabetic agents.