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Divergent Total Syntheses of Lyconadins A and C

Authors


  • We are grateful to Prof. P. Fuchs for generous gifts of chemicals and glassware. We thank Prof. Y. Xia’s group for MS assistance as well as Prof. Fukuyama and Prof. Yokoshima for experimental suggestions regarding the pyridone synthesis step. We thank the NYU Molecular Design Institute for the purchase of the Bruker SMART APEXII Diffractometer and Dr. Chunhua Hu for assistance with data collection and structure determination. Financial support from Purdue University, Purdue Center for Cancer Research, and Purdue Research Foundation is gratefully acknowledged. M.D. is a recipient of the 2013 ORAU Ralph E. Powe Junior Faculty Enhancement Award.

Abstract

Divergent and concise total syntheses of two lycopodium alkaloids, lyconadins A and C have been developed. The synthesis of lyconadin A, having potent neurotrophic activity, features an efficient one-pot ketal removal and formal aza-[4+2] cyclization to form the cagelike core structure. A tandem ketal removal/Mannich reaction was developed to build the tricyclic structure of lyconadin C. Both lyconadins A and C were synthesized from a pivotal intermediate.

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