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

Explore the groundbreaking total synthesis of Dynemicin A methyl esters with detailed steps and key contributions to science by Stuart L. Schreiber.

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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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