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Total Synthesis of (+)- Fastigiatine

Total Synthesis of (+)- Fastigiatine. Gretchen Peters February 10 , 2011. Shair Research Group. Total synthesis and chemical biology Focus of syntheses: “naturally occurring complex molecules that challenge the state-of-the-art of organic synthesis”

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Total Synthesis of (+)- Fastigiatine

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  1. Total Synthesis of (+)-Fastigiatine Gretchen Peters February 10, 2011

  2. Shair Research Group • Total synthesis and chemical biology • Focus of syntheses: “naturally occurring complex molecules that challenge the state-of-the-art of organic synthesis” • Complexes that are unique structurally and biologically http://www.chem.harvard.edu/research/faculty/matthew_shair/research/research.html

  3. Lycopodium alkaloids • Found in plants (clubmosses) • Members have been found to have cardiovascular and neuromuscular effects • Used for homeopathic remedies (-)-himeradine A (+)-fastigiatine lycodine http://findarticles.com/p/articles/mi_g2603/is_0004/ai_2603000497/

  4. Retrosynthesis 1,4 Addition Mannich Condensation

  5. Protection 2 1

  6. Cuperate Addition 2 3

  7. Alkylation, Decarboxylation 4 3 5

  8. Addition of Li-enolate 5 7 6

  9. Intramolecular Aza-Wittig 6 7

  10. Reactive Amine • Wanted to remove protecting group and induce addition • Free amine too reactive • Added on to a,b unsaturated ketone to form five-membered ring 7

  11. Acid catalyzed cyclization 8 7 9

  12. Mannich Reaction 9 10

  13. Conclusions • First synthesis of (+)-fastigiatine • 15 step synthesis with 30% overall yield

  14. Acknowledgements • Chem 647 classmates • Dr. Davis

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