Synthesis of 4-Aminocyclopentenones via Aza-Piancatelli - PowerPoint PPT Presentation

Synthesis of 4-Aminocyclopentenones via Aza-Piancatelli Rearrangements Using Polymer-Bound Metal Catalyst Teresa Garay University of California, Santa Barbara Undergraduate Researcher, UCLEADS 2010 25 August 2010

Introduction: Natural Products Taxus brevifolia Taxol Anti-cancer alkaloid http://courses.washington.edu/bot113/conifer_slides/ source/taxus_brevifolia.html  Need synthetic chemists to develop new methods to access biologically important molecules in the lab Wall, M.E. Med. Res. Rev. 1998 , 18 , 309. 2

Natural Products: A Sub-Family of Cyclopentane Motifs  New methods of forming a cyclopentane scaffold containing nitrogen Cephalotaxine NK 1 inhibitor 1  Continuous flow chemistry: importance to industry  “green” chemistry; more efficient and less waste http://www.californiagreensolutions.com /images/chemistry-globe.jpg 1 Finke, P.E. et al. Bioorg. Med. Chem. Lett. 2006 , 16, 4497-4499. 3

Where Are We Now?  The Piancatelli rearrangement 1  Aza-Piancatelli rearrangements of furylcarbinols with amines to afford 4-aminocyclopentenones 1 Piancatelli, G. et al. Tetrahedron Lett. 1976 , 39 , 3555. 4

Polymer-bound Lewis Acid Catalyst  Develop a comparative analysis: powder versus polymer-bound  yield catalytic activity  reaction efficiency  catalyst degradation   reaction time, etc. Powder scandium triflate catalyst OTf = triflate Polystyrene-bound scandium triflate catalyst 5

Materials  Two different furylcarbinols to react with p -iodoaniline  p -methoxyphenyl furylcarbinol phenyl furylcarbinol   Polystyrene-bound Scandium triflate catalyst beads 6

Laboratory Process Rotary Flash Column TLC NMR Evaporator Chromatography 7

Laboratory Process Rotary Flash Column TLC NMR Evaporator Chromatography S C R 8

Laboratory Process 12

p -Methoxyphenyl Furylcarbinol 13

Phenyl Furylcarbinol 14

Conclusion: What Does This Mean?  Comparable yields indicate similar catalytic activity of polymer-bound catalyst beads to powder catalyst  Catalyst beads can be recycled, as they show no degradation or instability after five trials  Consistent yields suggest catalyst bead tolerance to air exposure for various lengths of time, and repeated heating cycles at 80 °C  Potential for use of greater mole percentage to speed up rate of reaction 15

Future Direction  Short-Term: Use new reactants in the rearrangement: different furylcarbinols and nitrogen species  Mid-term: Investigate especially low-yielding reactions using polymer-bound catalyst in comparison to free, powder catalyst  Long-term: Build a continuous flow reactor using solid supported polymer-bound catalyst Reaction column Next steps in with immobilized synthesis catalyst 16

Acknowledgements  Dr. Javier Read de Alaniz and my mentor, Gesine Veits, for being patient and giving me the opportunity to contribute to their projects  Thank you to the rest of the Read de Alaniz group for sharing their space and knowledge Jarred Engelking, Charles Frazier, Leoni Palmer, and Donald Wenz   Arica Lubin and Matthew Crossley, and all the people who made this a program a success and a meaningful experience 17

Synthesis of 4-Aminocyclopentenones via Aza-Piancatelli - PowerPoint PPT Presentation

Synthesis of 4-Aminocyclopentenones via Aza-Piancatelli Rearrangements Using Polymer-Bound Metal Catalyst Teresa Garay University of California, Santa Barbara Undergraduate Researcher, UCLEADS 2010 25 August 2010 Introduction: Natural Products

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