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Ying Wang, Jelena Janjic , Sergey A. Kozmin

Discover the innovative approach of synthesizing Leucascandrolide A from commercially available precursors in a 18-step linear sequence. Learn about its structural features and bioactivity, including potent cytotoxicity and inhibitory effects on yeast. Follow the detailed retrosynthesis to understand the construction of its complex molecular framework.

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Ying Wang, Jelena Janjic , Sergey A. Kozmin

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  1. Synthesis of Leucascandrolide A via a Spontaneous MacrolactolizationJ. Am. Chem. Soc. 2002, 124, 13670-13671Presented by Vijayarajan Devannah3/19/2013 Ying Wang, JelenaJanjic, Sergey A. Kozmin

  2. About Professor Sergey A. Kozmin Education and Professional • 1991-1993 Undergraduate Research Assistant with Professor Irina P. Beletskaya Lomonosov Moscow State University, Moscow, Russia • 1993-1998 Graduate Research Assistant with Professor Viresh H. RawalUniversity of • Chicago, Chicago, Illinois • 1998-2000 Postdoctoral Associate with Professor Amos B. Smith, III University of Pennsylvania, Philadelphia, Pennsylvania • 2000-2006 Assistant Professor, University of Chicago • 2006-2011 Associate Professor, University of Chicago • 2011-present Professor, University of Chicago Notable Awards • 2003 Alfred P. Sloan Fellow • 2004 American Cancer Society Research Scholar • 2004 Amgen Young Investigator’s Award • 2004 Camille Dreyfus Teacher-Scholar Award • 2005 NSF CAREER Award • 2005 GlaxoSmithKline Chemistry Research Scholar

  3. About Leucascandrolide A • Its is a highly bioactive marine macrolide isolated from new genus of calcerous sponges Leucascandra caveolata. • It displays potent cytotoxicity against KB and P388 tumor cell lines ( IC50 50 ng/ml and 0.25 μg/mL respectively), and it also a strong inhibitor of animal-pathogenic yeast candida albicans. Structural Features of Leucascandrolide A • It possess a 14 membered lactone • It includes dioxotricyclic core • It is highly unsaturated and contains oxazole in its side chain.

  4. Retrosynthesis

  5. Synthesis of C1-C15 Fragment Scheme 2 Scheme 3

  6. Continues…… Scheme 4 Scheme 5

  7. Formation of crucial Macrocycle Scheme 5

  8. Synthesis of Oxazole side chain and completion of the target Leucascandrolide A Scheme 6

  9. Conclusion • Racemic Leucascandrolide A was synthesized in longest linear sequence of 18 steps from commercially available precursors. 500 MHz 1H NMR and 125 MHz 13C NMR spectra of synthetic Leucascandrolide A was in excellent agreement with those reported in literature. • Total yield is 2%

  10. Thank You

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