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

Beschreibung

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% 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.
Total synthesis of the bioactive natural products, pachastrissamine, lysergic acid, lysergol and isolysergol, by palladium-catalyzed domino cyclization of allenes and related compounds is investigated Gives an insight to the development of efficient synthetic approaches for biologically active compounds Nominated as an oustanding contribution by Kyoto University Includes supplementary material: sn.pub/extras

Autor*in

Shinsuke Inuki

Themen in »Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds«

allene cyclization bioactive natural products ergot alkaloid functionalized heterocycles naural products palladium-catalyzed cascade cyclization palladium-catalyzed domino cyclization total synthesis

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From the reviews:

“The target audience … includes practicing organic chemists with interests in synthesis, and those with specific interests in palladium-catalysed organic reactions, and as such is suited to graduate level and above. … is well-written and provides plenty of food for thought for specialists in palladium(II) chemistry … . the book also benefits from a comprehensive experimental section at the end of each chapter. … the book reflects the high quality experimental skills of the author, and provides a useful handbook for the synthetic organometallic chemist.” (Edward A. Anderson, Platinum Metals Review, Vol. 56 (3), 2012)

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