Type
Text
Type
Dissertation
Advisor
Johnson, Francis | Parker, Kathlyn A | Fowler, Frank | Lau, Roland.
Date
2015-08-01
Keywords
Chemistry
Department
Department of Chemistry.
Language
en_US
Source
This work is sponsored by the Stony Brook University Graduate School in compliance with the requirements for completion of degree.
Identifier
http://hdl.handle.net/11401/77081
Publisher
The Graduate School, Stony Brook University: Stony Brook, NY.
Format
application/pdf
Abstract
An efficient total synthesis of the novel squalene synthase inhibitor, bisabosqual A, is presented herein. The key step, a 5-exo, 6-exo tandem radical cyclization assembles the fully functionalized bisabosqual core, providing two rings and setting three stereogenic centers (two with complete specificity) in one step. Additional effective transformations include a regioselective deoxygentation reaction utilizing the Trost-Hutchins reducing system and a chemo- and diastereoselective addition of trimethylaluminum to an advanced ketone intermediate in the presence of esters. The doubly convergent synthesis requires 14 steps (longest linear sequence) from commercially available starting materials. | 292 pages
Recommended Citation
am Ende, Christopher William, "Total Synthesis of Bisabosqual A" (2015). Stony Brook Theses and Dissertations Collection, 2006-2020 (closed to submissions). 2918.
https://commons.library.stonybrook.edu/stony-brook-theses-and-dissertations-collection/2918