Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 15, Pages 3922-3925Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201400416
Keywords
alkaloids; cyclizations; drug discovery; natural products; total synthesis
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Funding
- Purdue University
- Purdue Center for Cancer Research
- Purdue Research Foundation
- ORAU Ralph E. Powe Junior Faculty Enhancement Award
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Divergent and concise total syntheses of two lycopodium alkaloids, lyconadinsA and C have been developed. The synthesis of lyconadinA, 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 lyconadinC. Both lyconadinsA and C were synthesized from a pivotal intermediate.
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