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Corey Basch Synthesis Presentation 4/30/13

Total Syntheses of (-)- Acutumine and (-)- Dechloroacutumine King, S. M.; Calandra , N. A.; Herzon , S. B. Angew . Chem. Int. Ed. 2013 , 52, 3642-3645. Corey Basch Synthesis Presentation 4/30/13. Seth Herzon. 2002 - B.S. Chemistry, Temple University.

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Corey Basch Synthesis Presentation 4/30/13

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  1. Total Syntheses of (-)-Acutumine and (-)-DechloroacutumineKing, S. M.; Calandra, N. A.; Herzon, S. B. Angew. Chem. Int. Ed.2013, 52, 3642-3645. Corey Basch Synthesis Presentation 4/30/13

  2. Seth Herzon 2002- B.S. Chemistry, Temple University. 2006- PhD Chemistry, Harvard University. 2008-2012- Assistant Professor of Chemistry, Yale University. 2012-Present- Associate Professor, Yale. 19 Publications (independent career) -Total synthesis of natural products -MOA and target identification of anticancer natural products -Methodology -Reagent development Awards: -Packard Fellowship -Sloan Fellowship -Cottrell Scholar Award -NSF Career Award -Eli Lilly New Faculty Award

  3. (-)-Acutumine/Dechloroacutumine (-)-Acutumine: - Isolated from Sinomeniumacutum. - Tetracyclic, spirocycle, 5 stereocenters. - Inhibits human T-cell proliferation. - Improves object/social recognition, memory in rat model. - Only one other total synthesis reported (Castle, 2009). (-)-Dechloroacutumine: - Isolated from Menispermumdauricum(Asian moonseed). - Direct metabolite of (-)-Acutumine. - No previously reported total synthesis. Menispermumdauricum

  4. Retrosynthesis

  5. Formation of the Arylacetylide from D-Ribose

  6. Addition of the Arylacetylide to the Bicyclic Core

  7. Hydrostannylation and Hosomi-Sakurai Allylation

  8. Setting the Oxidation State of the Spirocyclopentenone Ring and a Final Reduction

  9. Overview • Longest linear sequence: 23 steps • (-)-Acutumine: 0.43 % • (-)-Dechloroacutumine: 1.5 % • First reported total synthesis of (-)-Dechloroacutumine • Second reported total synthesis of (-)-Acutumine Thank you!

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