CHED 409 |
| A concise, flexible synthetic avenue was developed for the preparation of compounds with the structures related to those proposed for the novel marine-derived differential cytotoxins Psymberin and Irciniastatin A. These are effective human cancer and murine cell growth inhibitors (GI50 from 0.001 to < 0.0001 µg/mL). Our efforts led to their complete stereochemical assignment and the conclusion that Psymberin and Irciniastatin A are identical compounds. The retrosynthetic analysis envisioned joining three fragments to create the target molecule. Model reactions predicted an overall yield of 8.9%. During the synthesis of fragment C17-C25, our group was unable to remove the protecting PMB groups. By changing the protecting groups to benzoyl, a more efficient synthesis of the C17-C25 fragment (23.75% yield) was obtained. This intermediate was then successfully used in the total synthesis of the Psymberin natural product. |
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Chemical Education |