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Recemic marinopyrrole B by total synthesis

Recemic marinopyrrole B by total synthesis. Ping Cheng, Derrick L. J. Clive*, Shimal Fernandopulle and Zhenhua Chen Chem. Commun. , 2013 , 49, 558. Ailun Ma 2014. 1. 10. Author. BSc, PhD, Imperial College, London P ostdocto r, Harvard in R. B. Woodward ’ s group

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Recemic marinopyrrole B by total synthesis

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  1. Recemic marinopyrrole B by total synthesis Ping Cheng, Derrick L. J. Clive*, Shimal Fernandopulle and Zhenhua Chen Chem. Commun., 2013, 49, 558 Ailun Ma 2014. 1. 10

  2. Author • BSc, PhD, Imperial College, London • Postdoctor, Harvard in R. B. Woodward’s group • Professor, the Chemistry Department of the University of Alberta Derrick L. J. Clive Research Interest Natural Product Synthesis &New ReactionMethodology

  3. Background • Marinopyrrole B was isolated from Streptomyces speciesfromamarinesedimentin 2008 by William Fenical. • The marinopyrrole B possesses potent antibiotic activities against methicillin-resistantStaphylococcus aureus(MRSA),as well as cytotoxicity against a colon cancer cell line.

  4. Thesyntheticplan

  5. Thesynthetic route

  6. conclusion 1. Their route to marinopyrrole B deals with introduction of bromine at a very early stage and relies on the special reactivity ofallylic acetate11towards nucleophiles. 2. This reactivity is harnessed as a new method to construct a carbon chain appropriately functionalized for the key Paal–Knorr reaction that generates the second pyrrole ring.

  7. Thank you!

  8. Paal-Knorr reaction

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