Alkaloid Synthesis: (−)-α-Kainic Acid (Ohshima), Serpentine (Scheidt), (−)-Galanthamine ( Jia), (+)-Trigolutes B (Gong), Sarain A (Yokoshima/Fukuyama), DZ-2384 (Harran)

(−)-α-Kainic acid 3 is widely used in neuropharmacological studies. En route to 3, Takashi Ohshima of Kyushu University found (Chem. Eur. J. 2015, 21, 3937) that the intramolecular ene cyclization of 1 delivered 2 with high diastereocontrol. Karl A. Scheidt of Northwestern University set (Angew. Chem. Int. Ed. 2015, 54, 6900) the absolute configuration of 5 and so of serpentine 6 by the organocatalyzed cyclization of 4. This is the first total synthesis of that alkaloid. Yanxing Jia of Peking University prepared (Angew. Chem. Int. Ed. 2015, 54, 6255) the benzofuran 8 by the Pd-mediated cyclization of the alkyne 7. An organo­catalyzed intermolecular Michael addition set the absolute configuration of (−)-galanthamine 9. Liu-Zhu Gong of the University of Science and Technology of China assem­bled (Chem. Eur. J. 2015, 21, 8389) (+)-trigolutes B 13 by the organocatalyzed addition of 10 to 11 to give 12. Barry M. Trost of Stanford University employed (Chem. Sci. 2015, 6, 349) a similar strategy in a synthesis of (−)-perophoramidine (not illustrated). Satoshi Yokoshima and Tohru Fukuyama of Nagoya University showed (Angew. Chem. Int. Ed. 2015, 54, 7367) that on deprotection, 14 was converted to an eight-membered cyclic nitrone, that further cyclized to 15. This set the stage for the synthesis of sarain A 16. Patrick G. Harran of UCLA has extensively studied the complex alkaloid (−)-diazonamide A (not illustrated). Structural simplification and optimization of antimitotic activity led to the macrolactam DZ-2384 18. It is exciting that 18 could be prepared (Angew. Chem. Int. Ed. 2015, 54, 4818) on a multigram scale by selective electrochemical oxidation of the much simpler precursor 17.