Expanding the uses of the NCAL and finding the spectrum of substrates best
suited for such a transformation has been the main effort of my research. Previous
studies had focused on aldedydes as the requisite functionality that would provide the
needed electrophilicity in order to complete the aldol; however, recent advancements
have introduced ketones as a viable carbonyl. With an established protocol in hand, I set
out to explore various substrates that could yield Beta-lactones in good to moderate yields
such as amino acid derivatives, diones, and large cyclic formations as well as simple,
straight chain acids with varying groups Alpha to the ketone. In general, I was able to
establish a basic framework of substrates that are highly and/or moderately susceptible
towards the NCAL and current studies continue to further expand the scope.
In addition to making Beta-lactones, I investigated alkyl cuprates as soft
nucleophiles to afford addition at the Beta carbon yielding a variety of acids. Substrates for
cuprate additions have been expanded to bulkier and multi-cyclic Beta-lactones and applied
to the synthesis of a Merck IND intermediate. Additions to bi- and tri-chloro Beta-lactones
due to the presence of the resulting moity in natural products are currently being studied.
| Identifer | oai:union.ndltd.org:tamu.edu/oai:repository.tamu.edu:1969.1/ETD-TAMU-2676 |
| Date | 15 May 2009 |
| Creators | Matla, Andrea Slava |
| 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 |
Page generated in 0.0018 seconds