Semester

Spring

Date of Graduation

2022

Document Type

Thesis

Degree Type

MS

College

Eberly College of Arts and Sciences

Department

Chemistry

Committee Chair

Gregory Dudley

Committee Co-Chair

Margaret Hilton

Committee Member

Margaret Hilton

Committee Member

Brian Popp

Abstract

Fragmentation methodology has been used in organic synthesis to produce complex organic compounds. This work is focused on fragmentation reactions leading to the subsequent construction of neopentylene-fused carbocycles, which are found in several important natural products and are difficult to prepare. These are produced by utilizing an optimized fragmentation methodology from the Dudley group. The methodologies build starting materials called nonaflates and triflates with a gem-dimethyl substituent that is seen in many natural products. Nonaflates and triflates are similar in structure, but nonaflates pose benefits that are an advantage over triflates, like cost effective synthesis and more stable compounds. A large-scale synthetic pathway was developed for 1,6-enynes which can be used for reaction discovery and target-oriented synthesis. 1,6-Enynes are also useful for cyclotrimerizations with various metal catalysts. Optimization of the one pot nonaflation synthesis of 3,3-dimethyl-5-hexyn-1-ol is important for natural product synthesis because 3,3-dimethyl-5-hexyn-1-ol is an ideal starting material for multiple synthetic targets because it has the gem-dimethyl substituent from which one can craft the neopentylene ring fusion into polycyclic target structures.

Download

Share

COinS