| Publication Type |
dissertation |
| School or College |
College of Science |
| Department |
Chemistry |
| Author |
Rohanna, John C. |
| Title |
Total synthesis of brevenal; synthesis of the AB- and E- ring subunits of brevenal and studies of olefinic-lactone ring-closing metathesis using a reduced titanium alkylidene; synthesis of (R)-(-)-muscone and (R)-(+)-muscopyridine |
| Date |
2011-05 |
| Description |
This dissertation describes the total synthesis of the marine ladder toxin brevenal utilizing a convergent synthetic strategy. Critical to the success of this work was the use of olefinic-ester cyclization reactions and the utilization of glycal epoxides as precursors to C-C and C-H bonds. Previous total syntheses of brevenal and our strategy for the completion of the molecule are discussed in detail. In addition, olefinic-lactone cyclization reactions that result in the generation of macrocycles are described. The methodology was used to synthesize the natural products muscone and muscopyridine. |
| Type |
Text |
| Publisher |
University of Utah |
| Subject |
Brevenal; Synthesis; Marine toxins; Marine ladder toxin; Brevetoxins; Red tide; Karenia brevis; Convergent synthetic strategy; Olefin-ester cyclization; Olefin-lactone cyclization |
| Dissertation Institution |
University of Utah |
| Dissertation Name |
Doctor of Philosophy |
| Language |
eng |
| Rights Management |
Copyright © John C. Rohanna 2011 |
| Format Medium |
application/pdf |
| Format Extent |
9,518,982 bytes |
| Identifier |
us-etd3,32756 |
| Source |
Original housed in Marriott Library Special Collections, QD3.5 2011 .R64 |
| ARK |
ark:/87278/s66d67q3 |
| Setname |
ir_etd |
| ID |
194286 |
| Reference URL |
https://collections.lib.utah.edu/ark:/87278/s66d67q3 |
