CHED 238 |
| Abstract: The proposed research project targets the synthesis of polyphenolic natural products and their analogues. The recent synthesis of Chiricanine A has provided some insight into the synthesis of more complex polyphenolic stillbenoids. This simple molecule can provide us with a synthetic model for Mappain, a cytotoxic compound isolated from Macaranga mappa. The first half of the synthetic steps will utilize the same methodologies as Schweinfurthin C, a geranylated stillbene which has the same structural features on the left side of the molecule as does Mappain. The synthesis of this portion of the molecule is proposed to occur in 10 steps. The starting point for this synthesis is 3,4-dihydroxybenzaldehyde, and with the exception of the bromination of this compound, all steps have proceeded in no less than 88%. First attempts at incorporation of the geranyl chain (J. Org. Chem. 1999, 64, 8718-8723) were unsuccessful. Another methodology allowing for Pd catalyzed reactions of allylic halides with a benzylic Grignard reagent has been utilized (J. Org. Chem. 2002, 67, 1167-1170). Future steps will look into the Wittig methodology to incorporate this side of the molecule.
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Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Poster
Division of Chemical Education |
