Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds (Springer Theses)

The author has developed novel methodologies for highly efficient construction of functionalized heterocycles by palladium-catalyzed domino/cascade cyclization of allenes and related compounds containing appropriate nucleophilic group(s). Based on these methodologies, enantioselective total syntheses of bioactive natural products, pachastrissamine (26% overall yield in seven steps), lysergic acid (4.0% overall yield in fifteen steps), lysergol (3.6% overall yield in fifteen steps) and isolysergol (8.2% overall yield in eleven steps) have been achieved. These are more facile synthetic route than those previously reported. These findings would contribute to the development of efficient synthetic methods for biologically active compounds containing a complex structure. The author has developed novel methodologies for highly efficient construction of functionalized heterocycles by palladium-catalyzed domino/cascade cyclization of allenes and related compounds containing appropriate nucleophilic group(s). Based on these methodologies, enantioselective total syntheses of bioactive natural products, pachastrissamine (26 per cent overall yield in seven steps), lysergic acid (4.0 per cent overall yield in fifteen steps), lysergol (3.6 per cent overall yield in fifteen steps) and isolysergol (8.2 per cent overall yield in eleven steps) have been achieved. These are Front Matter....Pages i-xvi Introduction....Pages 1-8 Front Matter....Pages 9-9 Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Bromoallenes....Pages 11-27 Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Propargyl Chlorides and Carbonates....Pages 29-49 Front Matter....Pages 51-51 Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group and Its Application to Total Synthesis of Ergot Alkaloids....Pages 53-75 Total Synthesis of (+)-Lysergic Acid, (+)-Lysergol, and (+)-Isolysergol....Pages 77-103 Conclusions....Pages 105-106 Annotation This text details efficient synthetic approaches for biologically active compounds. It describes novel methodologies for highly efficient construction of functionalized heterocycles by palladium-catalyzed domino cyclization of allenes and related compounds