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Presented by Andrew Cinderella

Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

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Page 1: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Presented by Andrew Cinderella

Page 2: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Samuel Danishefsky� Born 1936 in Bayonne, NJ� B.S. from Yeshiva University 1956� PhD from Harvard 1962� NIH post-doc fellow at Columbia, Stork Lab� 1963-1980 University of Pittsburg� 1963-1980 University of Pittsburg� 1980-1993 Yale University� 1993-present Columbia UniversityAwards� Wolf Prize in Chemistry with Stork� Arthur C. Cope Award� Benjamin Franklin Medal in Chemistry� National Academy of Science’s Award in Chemistry� >480 publications

Page 3: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Dynemicin A� Possible anti-tumor agent

� Binds to the minor-groove of the DNA double helix

� Most effective in rapid growth cells

Page 4: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Retrosynthesis

Page 5: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Approach

Page 6: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Early Synthetic Steps

Page 7: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Approach

Page 8: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Attempted Routes

Page 9: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Approach

Page 10: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Path II Synthetic Steps

Page 11: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Path II Synthetic Steps Cont.

Page 12: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Approach

Page 13: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Final Synthetic Steps

Page 14: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Conclusion� Dynemicin A was successfully synthesized in 33 steps.

� Overall yield of 0.13%

Page 15: Presented by Andrew Cinderella - University of Delaware · 2013-02-12 · Presented by Andrew Cinderella. Samuel Danishefsky Born 1936 in Bayonne, NJ B.S. from Yeshiva University

Questions???Thank you!!!