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

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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
Publication Type dissertation
School or College College of Science
Department Chemistry
Author Rohanna, John C.
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 application/pdf
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
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