Document Type

Dissertation

Degree

Doctor of Philosophy

Major

Chemistry, Organic

Date of Defense

11-23-2020

Graduate Advisor

Prof. Christopher D. Spilling, Ph.D.

Committee

Prof. Eike B. Bauer, Ph.D.

Prof. James S. Chickos, Ph.D.

Prof. Janet B. Wilking, Ph.D.

Abstract

This work has been divided into two major projects:

1) Synthesis of phosphonomethyl tetrahydrofurans by using the Mori-Tamaru reaction: The Mori-Tamaru reaction of phosphonate-substituted dienes is unexplored, and the directing effects of the phosphono-group are uncertain. The objectives of this research are to develop the homoallylation of phosphonodienes with different aldehydes, followed by their cyclization to phosphonomethyl tetrahydrofuran ring systems through an oxa-Michael reaction. This method has also been applied for the synthesis of 3-hydroxy substituted phosphonomethyl tetrahydrofuran rings (9) which might lead to the synthesis of 2’deoxy C-nucleosides.

2) Synthesis of vinyl phosphonates and phostones: Synthetic approaches for phostones are still not fully explored. A recent study of some examples of biologically active phostone derivatives demonstrated that there is a need for additional versatile approaches to phostone synthesis. We have developed a new synthetic approach for phostones starting from readily available starting materials. Our approach to the synthesis of phostones involves the formation of vinyl phosphonates followed by reduction to saturated δ-hydroxy phosphonates, which on cyclization results in phostones.

Available for download on Saturday, December 11, 2021

Additional Files

6. 3MT-2018-UMSL.ppt (1489 kB)
3 MT competition slide

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