Carbohydrate-Based Strategy for the Synthesis of Zaragozic Acid via a Novel Lewis Acid-Mediated Reaction of an α-Acetoxy Sulfide
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The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).
History
The Department of Chemistry was founded in 1880.
Dates of Existence
1880-present
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- College of Liberal Arts and Sciences (parent college)
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Abstract
Zaragozic acid A (1) is a natural product isolated from Sporormiella intermedia and Leptodonitium elatius.' It is an important synthetic objective because it is a competitive inhibitor of squalene synthasea2 Its inhibition at the picomolar level makes it a promising candidate in the search for drugs that regulate cholesterol levels. A few synthetic approaches to the 2,8-dioxabicyclo- [3.2.lloctane skeleton have been ~ommunicated.~ As part of our continuing interest in bridged compounds,4 we sought an efficient route to a suitably functionalized bicyclic intermediate and report herein the direct synthesis of diol 2.
Comments
Reprinted (adapted) with permission from The Journal of Organic Chemistry,60(1); 2-3. Doi: 10.1021/jo00106a001. Copyright 1995 American Chemical Society.