Total Syntheses of Di- and Tri-O-methyl Dynemicin A Methyl Esters Jack Taunton, John L. Wood, and Stuart L. Schreiber Department of Chemistry, Harvard University Presented by Scott Shuler

Stuart L. Schreiber B.A. in Chemistry from University of Virginia in 1977 PhD in Organic Chemistry from Robert Woodward and Yoshito Kishi at Harvard University Assistant Professor at Yale University in Returned to Harvard in 1988 as a member of the Department of Molecular and Cellular Biology Founded the Harvard Institute of Chemistry and Cell Biology, which subsequently merged with MIT's Center for Genome Research in Schreiber currently resides at Harvard under numerous roles and job titles. 1

Major Contributions to Science Total synthesis of talaromycin B, asteltoxin, avenaciolide, gloeosporone, hikizimicin, mycoticin A, epoxydictymene and the immunosuppressant FK- 506.FK- 506 Development of a systematic use of small molecules as biological probes. Development of four anti-cancer drugs: torisel (1994), afinitor (1994), vorinostat (1996), and romidepsin (1996). Co-founded four biopharmaceutical companies (Vertex Pharmaceuticals, ARIAD Pharmaceuticals, ARIAD Gene Therapeutics, and Infinity Pharmaceuticals). 2 Source:

Dynemicin A Dynemicin A has preliminarily been found to be an anti-cancer agent 1 ; as a result, it has become an increasingly popular target for pharmaceutical and biological research. Subsequently, this makes it a sought after target in total synthesis. 3 1) Source:

Retrosynthesis 4

Synthesis: Steps Source: Porco, J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. Journal of the American Chemical Society 1990, 112, 7410.

Synthesis: Steps Source: Wood, J. L.; Porco, J. A.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. Journal of the American Chemical Society 1992, 114, 5898.

Synthesis: Steps Total Yield = % Source: Taunton, J.; Wood, J. L.; Schreiber, S. L. Journal of the American Chemical Society 1993, 115,

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