Identifier
etd-07042016-113601
Degree
Doctor of Philosophy (PhD)
Department
Chemistry
Document Type
Dissertation
Abstract
This dissertation describes strategies for synthesizing prostaglandin PGF2α. Our synthetic design creates the stereochemistry needed for the core and side chains of the target prostaglandin PGF2 alpha and PGF2 alpha synthase selective analogues while incorporating iodocyclization desymmetrization of acyclic dienes. A model system for 4-(iodomethyl)-6-methyl-1,3-dioxan-2-one was developed and synthesized for our target compound 4-(2-(benzyloxy)ethyl)-6-(iodomethyl)-5-vinyl-1,3-dioxan-2-one. Both compounds were successfully synthesized providing useful stereocenters for completing the synthesis of prostaglandin PGF2 alpha. Efforts toward total stereochemical control of PGF2α include the partial syntheses of bis-diethylanimedimethylsilane and of (4S,5S)-2-((1E,3E)-penta-1,3-dien-1-yl)-4,5-diphenyl-1,3-ditosyl-1,3,2-diazaborolidine.
Date
2016
Document Availability at the Time of Submission
Release the entire work immediately for access worldwide.
Recommended Citation
Pollard, Amy Marie, "Synthetic Efforts Towards the Synthesis of Prostaglandin PGF2a" (2016). LSU Doctoral Dissertations. 2719.
https://repository.lsu.edu/gradschool_dissertations/2719
Committee Chair
Crowe, William
DOI
10.31390/gradschool_dissertations.2719