Covering: 2000 to 2021Lignan natural products are found in many different plant species and possess numerous useful biological properties, such as anti-inflammatory, antiviral, antioxidant, antibacterial, and antitumor activities. Their utility in both traditional and conventional medicine, coupled with their structural diversity has made them popular synthetic targets over many decades. This review specifically addresses the cyclolignan subclass of the family, which possess both a C8-C8' and a C2-C7' linkage between two different phenylpropene units. We present a comprehensive overview of the diverse strategies employed by chemists to achieve enantioselective total syntheses of cyclolignans covering: 2000 to 2021.