Synthetic Studies on Pseudo‐Dimeric Lycopodium Alkaloids: Total Synthesis of Complanadine B

Abstract

Two approaches to the total synthesis of the dimeric Lycopodium alkaloid complanadine B have been achieved. In the first approach (see scheme; route 1), a keto lycodine unit is coupled to another lycodine unit whereas in the latter approach (route 2), selective oxygenation of one of two pseudo‐benzylic positions is achieved.

Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation

“…We describe here an efficient and enantioselective approach to tetracyclic lactone 9 representing a key motif toward the synthesis of various neurotrophic [103–110] Illicium sesquiterpenes. Key to the strategy was a highly enantioselective Robinson annulation reaction that proceeded under organocatalytic conditions to form the Hajos–Wiechert-like enone 8 .…”

Synthesis of Natural Products and Pharmaceuticals via Catalytic CH Functionalization

“…The Suzuki-Miyaura cross-coupling of 173 with triflate 174 then led to complanadine A in a total of eight steps. In 2013, the Sarpong group has also accomplished the synthesis of complanadine B, a congener of complanadine A, using a similar strategy [78].…”

Competent Route to Unsymmetric Dimer Architectures: Total Syntheses of (−)‐Lycodine and (−)‐Complanadines A and B, and Evaluation of Their Neurite Outgrowth Activities

“…Total synthesis of 4 was recently reported by the groups of Sarpong and Siegel . Sarpong and co‐workers also reported a total synthesis of 5 , whereas the Lewis group reported a synthetic study toward complanadines . We were also interested in the syntheses of 1 and its unsymmetric dimers 4 and 5 , because dimeric alkaloids often show distinct and/or improved biological activities compared to those of the monomer .…”