The pyrrole-imidazole alkaloid family of natural products illustrates the diversity
of topographically unique molecules with potent biological activities that can be found
in the marine environment. Thus, great interest for this class of compounds has
developed leading to new synthetic methodologies and tactics to build these complex
secondary metabolites.
The overall objectives of this research project include the total synthesis of the
phakellins and phakellstatins. First, we revisited the strategy developed in our group for
the total synthesis of (+)-dibromophakellstatin and utilized it for the synthesis of its
naturally occurring enantiomer and congeners. Second, we proposed and studied a new
and more concise approach to the phakellstatins and phakellins based on a key C-H
insertion process developed by Du Bois. Attempts to streamline the first synthesis of (+)-dibromophakellstatin proved to
be quite challenging. Shortcomings in the reproducibility of some parts of the original
strategy precluded us from completing and making more efficient the synthesis of the
natural enantiomer (-)-dibromophakellstatin. Fortuitously, our second generation
approach though it presented itself as an efficient route to the phakellins and
phakellstatins produced the undesired anti diastereomer of the key guanidine
intermediate which precluded our study of the pivotal C-H insertion reaction.
| Identifer | oai:union.ndltd.org:tamu.edu/oai:repository.tamu.edu:1969.1/ETD-TAMU-1255 |
| Date | 15 May 2009 |
| Creators | Franco-Torres, Francisco Miguel |
| Contributors | Romo, Daniel |
| Source Sets | Texas A and M University |
| Language | en_US |
| Detected Language | English |
| Type | Book, Thesis, Electronic Thesis, text |
| Format | electronic, application/pdf, born digital |
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