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Studies toward the total synthesis of pentalenic acid

Steven M. Reister-2015-05-12-Montana State University ScholarWorks (Montana State University)

TL;DRAbstract

The intent of the research contained herein was to synthesize the natural product pentalenic acid.Pentalenic acid is a small molecule with antibiotic properties.This molecule was chosen as a way to showcase ongoing synthetic methodologies of the Grieco research group.Unfortunately the complete synthesis of pentalenic acid was never realized, but the research proved to be both interesting and surprising.The original route proposed for a key intermediate was much more of a synthetic challenge than was anticipated.In fact it was eventually decided that the desired intermediate could not be obtained via this route and an alternative route was sought after.The alternative route proposed was successful and the desired intermediate was obtained in the same number of synthetic steps as the original.With this intermediate in hand, the key step in the synthesis was performed with rather surprising results.The major product obtained was not the desired one.In fact it was found that the reaction h

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The intent of the research contained herein was to synthesize the natural product pentalenic acid.Pentalenic acid is a small molecule with antibiotic properties.This molecule was chosen as a way to showcase ongoing synthetic methodologies of the Grieco research group.Unfortunately the complete synthesis of pentalenic acid was never realized, but the research proved to be both interesting and surprising.The original route proposed for a key intermediate was much more of a synthetic challenge than was anticipated.In fact it was eventually decided that the desired intermediate could not be obtained via this route and an alternative route was sought after.The alternative route proposed was successful and the desired intermediate was obtained in the same number of synthetic steps as the original.With this intermediate in hand, the key step in the synthesis was performed with rather surprising results.The major product obtained was not the desired one.In fact it was found that the reaction h

Keywords

Total synthesisChemistryStereochemistry

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