ORGN 338 |
Structural diversity via the solid-phase Nenitzescu indole synthesis
| Daniel M. Ketcha and Christine E. Charlesworth. Department of Chemistry, Wright State University, 3640 Colonel Glenn Hwy, Dayton, OH 45435 |
In our previous study, it was determined that the Nenitzescu indole synthesis could be performed on the solid-phase via initial acetoacetylation of a Rink-NH2 resin with diketene followed by the addition of an amine and quinone. We now find that in changing solvents from nitromethane to formamide, this reaction could be effected upon ester linked resins including Wang supported amino acids. Furthermore, subsequent manipulations upon this scaffold, such as Mitsunobu reactions at the C-5 hydroxyl group as well as Pd-mediated processes upon halide groups on the benzenoid lead to highly diverse indole-peptide hybrids. The scope and limitations of such diversity creating reactions will be discussed. |
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Physical Organic, Combinatorial, Materials, Molecular Recognition
8:00 PM-10:00 PM, Tuesday, March 30, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
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