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Total Syntheses of Di- and Tri-O-methyl Dynemicin A Methyl Esters

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

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Total Syntheses of Di- and Tri-O-methyl Dynemicin A Methyl Esters

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  1. 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

  2. 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 1981. • 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 2003. • Schreiber currently resides at Harvard under numerous roles and job titles.

  3. Major Contributions to Science • Total synthesis of talaromycin B, asteltoxin, avenaciolide, gloeosporone, hikizimicin, mycoticin A, epoxydictymene and the immunosuppressant 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). Source: http://www.broadinstitute.org/chembio/lab_schreiber/members/smdbSchreiberBio.php

  4. Dynemicin A • Dynemicin A has preliminarily been found to be an anti-cancer agent1; 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. 1) Source: http://en.wikipedia.org/wiki/Dynemicin_A

  5. Retrosynthesis

  6. Synthesis: Steps 1-6 Source: Porco, J. A.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. Journal of the American Chemical Society 1990, 112, 7410.

  7. Synthesis: Steps 7-21 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.

  8. Synthesis: Steps 22-31 Source: Taunton, J.; Wood, J. L.; Schreiber, S. L. Journal of the American Chemical Society 1993, 115, 10378. Total Yield = 0.16635%

  9. Fin

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