Asymmetric Total Synthesis of the Antiviral Natural Product (+)- Sattazolin

DeSouchet, Aimee L. and Doty, Trevor S. and Miller, Dr. Kenneth A. (2013) Asymmetric Total Synthesis of the Antiviral Natural Product (+)- Sattazolin. [Abstract]

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Abstract

Sattazolin is a natural product produced by the soil bacteria Bacillus sp. along with other structurally related acyloins sattabacin and 4-hydroxysattabacin. Our research group has previously reported the asymmetric total syntheses of sattabacin and 4-hydroxysattabacin, while the total synthesis of sattazolin had not been reported. Further, the isolation chemists reported an optical rotation for sattazolin but failed to determine the absolute configuration of the hydoxyl bearing stereocenter. Thus, its asymmetric total synthesis was undertaken both to access useful quantities of sattazolin and to determine the absolute configuration of the natural product. This poster describes the completion of the total synthesis of (+)-sattazolin, which allowed for the absolute stereochemistry to be unambiguously assigned. This work finally allows for the preparation of significant quantities of (+)-sattazolin that will be used to study the unique mechanism by which these compounds inhibit viral growth.

Item Type: Abstract
Created by Student or Faculty: Student
Additional Information: 8th Annual Natural & Behavioral Sciences Undergraduate Research Symposium Program
Uncontrolled Keywords: Sattazolin, Asymmetric Total Synthesis, soil bacteria, optical rotation, absolute configuration
Subjects: School of Natural and Behavioral Sciences > Chemistry
School of Natural and Behavioral Sciences > Environmental Studies
School of Natural and Behavioral Sciences > Geosciences
NBS Symposium
Depositing User: Alejandro Marquez
Date Deposited: 10 May 2013 13:15
Last Modified: 10 May 2013 13:15
URI: http://eprints.fortlewis.edu/id/eprint/227


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