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Total Synthesis of: (-) Mersicarpine by 74Qqr67h

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									Total Synthesis of:
(-) Mersicarpine




     Research: Tohru Fukuyama
     Presentation: Carl Brothers
               Tohru Fukuyama
• Chemistry Professor at
  University of Tokyo in
  Japan
  – Graduate school of
    Pharmaceutical
    Sciences
  – Synthetic Natural
    Products chemistry
• Discovered Fukuyama
  Coupling in 1998
       Fukuyama Coupling
• Coupling between a thioester and an
  organozinc halide in the presence of a
  palladium catalyst.
  – Mild reaction conditions
  – High chemoselectivity
  – Less toxic reagents
  – Stops at ketone
                 Mersicarpine
• Found in the stem-bark
  extract of the Malayan K.
  arborea.
  – Also found in other Kopsia.
• A small tree with waxy
  leaves, white flowers, and
  dark fruit.
• Found in lowland rainforests
  and beach forests close to
  the sea throuought southeast
  Asia and parts of Australia.
               Mersicarpine
•   Indole alkaloid.
•   Biological activity?
•   Medicinal uses?
•   Similar
    compounds show
    anti- cancer and
    anti- HIV activity.
          Retrosynthetic Analysis

              Oxidation




cyclization


                          Sonogashira
                          Coupling

                                        Eschenmoser-Tanabe
                                        Fragmnetation
Synthesis of “starting material”




           32%                                  77%,
                                                87% ee
                     Semicarbazide hydrochloride,
                     sodium acetate,
                     ethanol
    9, 44%, 99% ee
                     0 C, 24 h
Total Synthesis


                  72%




                  87%
88%




60%
87%




78%




78%
               97%




               76%




96%, 1.34% from
cyclohexanone
42 mg of final product

								
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