1. Controlled oligomerization via iterative Diels-Alder cycloadditions on solid supports. 2. Synthetic studies towards the total synthesis of hetisine and synthesis of the tricyclic core of sarain A [electronic resource].
- Chemistry, Organic
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- This dissertation describes two independent research projects. First part describes the modification and application of tandem Diels-Alder methodology to the synthesis of the oligomeric compound on solid support. Controlled Iterative Diels-Alder cycloadditions were nicely employed confirming the viability of this approach to the synthesis of oligomeric compounds.
Second part described herein illustrates our synthetic studies towards the total synthesis of hetisine alkaloids utilizing Winkler group's methodology involving the photocycloaddition of vinylogous amides. Problems occurred in the intramolecular photocycloaddition for the construction of the tetracyclic ring system in our initial synthetic approach, which motivated us to develop a new methodology involving a crossed photocycloaddition of vinylogous, amides leading to the formation of compounds bearing 6-azabicyclo[3.2.1]octane ring system. This new methodology was successfully applied to the construction of the ABE tricyclic ring system of hetisine with remarkable stereoselectivity. Successful synthesis of 6-azabicyclo[3.2.1]octan-3-one and the tricyclic ring system embedded in hetisine alkaloids confirmed the utility of our new methodology.
In addition, the synthesis of the tricyclic core of sarain A was successfully achieved utilizing this methodology in a remarkably efficient sequence. These successful construction of numerous ring systems in natural compounds attests to the utility of this new photochemical sequence developed in our laboratory.
- Source: Dissertation Abstracts International, Volume: 62-11, Section: B, page: 5124.
Supervisor: Jeffrey D. Winkler.
Thesis (Ph.D.)--University of Pennsylvania, 2001.
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- School code: 0175.
- University of Pennsylvania.
- Contained In:
- Dissertation Abstracts International 62-11B.
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- Restricted for use by site license.
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